[ CAS No. 1138-80-3 ] {[proInfo.proName]}

Name: 1138-80-3|2-(((Benzyloxy)carbonyl)amino)acetic acid|98%
Brand: Ambeed
SKU: A141974
Price: 5.0 USD
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2D 3D

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Quality Control of [ 1138-80-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1138-80-3 ]

Product Details of [ 1138-80-3 ]

CAS No. :	1138-80-3	MDL No. :	MFCD00002691
Formula :	C₁₀H₁₁NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CJUMAFVKTCBCJK-UHFFFAOYSA-N
M.W :	209.20	Pubchem ID :	14349
Synonyms :	N-Carboxyglycine N-benzyl ester;N-(α-Carbobenzoxy)glycine;Carbobenzoxyglycine;N-Benzyloxycarbonylglycine;N-(Carbobenzyloxy)glycine;N-(Carbobenzoxy)glycine;N-(Benzyloxycarbonyl)glycine;Z-Glycine	Chemical Name :	2-(((Benzyloxy)carbonyl)amino)acetic acid

Calculated chemistry of [ 1138-80-3 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.2
Num. rotatable bonds :	6
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	52.08
TPSA :	75.63 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.03
Log Po/w (WLOGP) :	0.85
Log Po/w (MLOGP) :	0.86
Log Po/w (SILICOS-IT) :	0.58
Consensus Log Po/w :	0.98

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.69
Solubility :	4.31 mg/ml ; 0.0206 mol/l
Class :	Very soluble
Log S (Ali) :	-2.21
Solubility :	1.3 mg/ml ; 0.00619 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.33
Solubility :	0.983 mg/ml ; 0.0047 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.02

Safety of [ 1138-80-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1138-80-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1138-80-3 ]
Downstream synthetic route of [ 1138-80-3 ]

[ 1138-80-3 ] Synthesis Path-Upstream 1~15

1
[ 1138-80-3 ]
[ 1160-54-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 501 - 517
[2] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 12, p. 3253 - 3260
[3] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 584 - 589
[4] Chemistry - A European Journal, 2012, vol. 18, # 9, p. 2632 - 2638

2
[ 6066-82-6 ]
[ 1138-80-3 ]
[ 2899-60-7 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 15, p. 2443 - 2449
[2] Journal of Mass Spectrometry, 2010, vol. 45, # 2, p. 178 - 189
[3] Tetrahedron Letters, 1995, vol. 36, # 12, p. 2105 - 2108
[4] Journal of Medicinal Chemistry, 1986, vol. 29, # 10, p. 1922 - 1929
[5] Journal of Medicinal Chemistry, 1991, vol. 34, # 6, p. 1845 - 1849
[6] Journal of Medicinal Chemistry, 1986, vol. 29, # 6, p. 912 - 917
[7] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 13, p. 1543 - 1546
[8] Tetrahedron Letters, 1997, vol. 38, # 17, p. 3039 - 3042
[9] Chemistry - A European Journal, 2004, vol. 10, # 16, p. 3879 - 3890
[10] Patent: US6423869, 2002, B1,
[11] Synlett, 2009, # 8, p. 1233 - 1236
[12] Tetrahedron Letters, 2012, vol. 53, # 6, p. 623 - 626
[13] Patent: WO2006/127702, 2006, A2, . Location in patent: Page/Page column 76

3
[ 1138-80-3 ]
[ 2899-60-7 ]

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 9, p. 1661 - 1664

4
[ 1138-80-3 ]
[ 107960-02-1 ]
[ 2899-60-7 ]

Reference： [1] Journal of Organic Chemistry, 1987, vol. 52, # 12, p. 2364 - 2367

5
[ 6066-82-6 ]
[ 598-45-8 ]
[ 1138-80-3 ]
[ 2899-60-7 ]

Reference： [1] Patent: US3933783, 1976, A,

6
[ 74124-79-1 ]
[ 1138-80-3 ]
[ 2899-60-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5559 - 5562

7
[ 21760-98-5 ]
[ 1138-80-3 ]
[ 1963-21-9 ]

Reference： [1] Chemische Berichte, 1975, vol. 108, p. 2680 - 2692

8
[ 1138-80-3 ]
[ 68-12-2 ]
[ 1857-19-8 ]

Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 15, p. 1765 - 1773

9
[ 1138-80-3 ]
[ 2304-94-1 ]

Reference： [1] Helvetica Chimica Acta, 2006, vol. 89, # 11, p. 2611 - 2637

10
[ 1138-80-3 ]
[ 77987-49-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
[2] Synthesis, 1990, p. 299 - 301
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 7, p. 858 - 864
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 26, p. 4874 - 4880

11
[ 1138-80-3 ]
[ 54755-77-0 ]

Reference： [1] Antimicrobial Agents and Chemotherapy, 2017, vol. 61, # 3,

12
[ 1138-80-3 ]
[ 39608-31-6 ]

Reference： [1] Patent: US4535167, 1985, A,

13
[ 7647-01-0 ]
[ 1138-80-3 ]
[ 1145-81-9 ]
[ 623-33-6 ]

Reference： [1] Journal of the American Chemical Society, 1944, vol. 66, p. 951,956

14
[ 7647-01-0 ]
[ 1138-80-3 ]
[ 623-33-6 ]

Reference： [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1937, vol. 247, p. 227,234
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 951,956

15
[ 1138-80-3 ]
[ 105258-93-3 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 16, p. 2277 - 2280

[ 1138-80-3 ] Synthesis Path-Downstream 1~88

1
[ 186581-53-3 ]
[ 1138-80-3 ]
[ 1212-53-9 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 87 - 93
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 24 - 30
[3]Helvetica Chimica Acta,1955,vol. 38,p. 1342,1345
[4]Bulletin de la Societe Chimique de France,1975,p. 793 - 799

3
[ 75-44-5 ]
[ 118-58-1 ]
[ 1138-80-3 ]
[ 116601-30-0 ]

Reference： [1]Helvetica Chimica Acta,1957,vol. 40,p. 604,606, 608

4
[ 35418-07-6 ]
[ 1138-80-3 ]
[ 79-22-1 ]
[ 102182-02-5 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 4639,4641

5
[ 2393-17-1 ]
[ 1138-80-3 ]
[ 79-22-1 ]
[ 102081-84-5 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 4639,4641

6
[ 1138-80-3 ]
[ 2566-19-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1951,vol. 572,p. 190,193
[2]Zhurnal Obshchei Khimii,1956,vol. 26,p. 2325,2328; engl. Ausg. S. 2601, 2603
[3]Chemische Berichte,1958,vol. 91,p. 1562,1566
[4]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 2592 - 2597
[5]Journal of the American Chemical Society,1980,vol. 102,p. 4537 - 4538
[6]Journal of the American Chemical Society,1980,vol. 102,p. 4537 - 4538
[7]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 2787 - 2790
[8]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2357 - 2359
[9]Justus Liebigs Annalen der Chemie,1951,vol. 572,p. 96,105
[10]Chemische Berichte,1958,vol. 91,p. 1073,1079
[11]Recueil des Travaux Chimiques des Pays-Bas,1959,vol. 78,p. 487,499
[12]Australian Journal of Chemistry,1958,vol. 11,p. 360,364
[13]Zhurnal Obshchei Khimii,1953,vol. 23,p. 417,422;engl.Ausg.S.427,430
[14]Chinese Chemical Letters,2014,vol. 25,p. 659 - 662
[15]Journal of Medicinal Chemistry,2016,vol. 59,p. 3920 - 3934
[16]Journal of Medicinal Chemistry,2020,vol. 63,p. 295 - 308

7
[ 67-56-1 ]
[ 542-32-5 ]
[ 1138-80-3 ]
[ 7533-38-2 ]

Reference： [1]Chemische Berichte,1966,vol. 99,p. 1040 - 1048

8
[ 50903-99-6 ]
[ 1138-80-3 ]
[ 81666-53-7 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1961,vol. 642,p. 145 - 162

9
[ 64-17-5 ]
[ 1138-80-3 ]
[ 1145-81-9 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 7072 - 7074
[2]Recueil des Travaux Chimiques des Pays-Bas,1964,vol. 83,p. 345 - 363
[3]Bulletin of the Chemical Society of Japan,1978,vol. 51,p. 1897 - 1898
[4]Pharmazie,1997,vol. 52,p. 203 - 206

10
[ 7512-17-6 ]
[ 1138-80-3 ]
[ 2292-98-0 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1965,p. 475 - 479
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1965,p. 496 - 502

11
[ 7364-42-3 ]
[ 1138-80-3 ]
[ 2566-19-0 ]

Reference： [1]Chemische Berichte,1961,vol. 94,p. 1263 - 1267

12
[ 22381-54-0 ]
[ 1138-80-3 ]
[ 21079-01-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1968,vol. 21,p. 2612 - 2617

13
[ 41844-56-8 ]
[ 1138-80-3 ]
[ 1212-53-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1974,vol. 47,p. 471 - 475

14
[ 21760-98-5 ]
[ 1138-80-3 ]
[ 1963-21-9 ]

Reference： [1]Chemische Berichte,1975,vol. 108,p. 2680 - 2692

15
[ 53386-64-4 ]
[ 1138-80-3 ]
N-(Benzyloxycarbonyl)-glycyl-N-benzyl-glycinmethylester [ No CAS ]

Reference： [1]Chemische Berichte,1968,vol. 101,p. 3623 - 3641

16
[ 1738-76-7 ]
[ 1138-80-3 ]
[ 19525-53-2 ]

Reference： [1]Tetrahedron,1982,vol. 38,p. 3267 - 3269
[2]Journal of Organic Chemistry,1962,vol. 27,p. 2091 - 2093
[3]Tetrahedron,1982,vol. 38,p. 3267 - 3269

17
[ 17288-15-2 ]
[ 1138-80-3 ]
[ 2420-10-2 ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 820 - 821

18
[ 66-84-2 ]
[ 1138-80-3 ]
[ 18831-79-3 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1967,vol. 348,p. 363 - 370

19
[ 4089-07-0 ]
[ 1138-80-3 ]
[ 3249-01-2 ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 2387 - 2394
[2]Bulletin of the Chemical Society of Japan,1965,vol. 38,p. 1979 - 1984
[3]Bulletin of the Chemical Society of Japan,1973,vol. 46,p. 3821 - 3824

20
[ 1138-80-3 ]
[ 56-40-6 ]
[ 2566-19-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1960,vol. 11,p. 153 - 164

21
[ 1138-80-3 ]
[ 459-73-4 ]
[ 2566-19-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1964,vol. 678,p. 148 - 159

22
[ 501-53-1 ]
[ 56-40-6 ]
[ 2566-19-0 ]
[ 1138-80-3 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 5375 - 5376

23
[ 46460-73-5 ]
[ 1138-80-3 ]
[ 97614-91-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1568 - 1574

24
[ 64113-91-3 ]
[ 1138-80-3 ]
[ 106880-81-3 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 1814 - 1826

25
[ 5557-81-3 ]
[ 1138-80-3 ]
[ 4066-24-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 1636 - 1641

26
[ 16741-80-3 ]
[ 1138-80-3 ]
[ 5908-08-7 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 4996 - 5002

27
[ 201274-07-9 ]
[ 1138-80-3 ]
[ 86088-51-9 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 2557 - 2563

28
[ 37993-32-1 ]
[ 1138-80-3 ]
[ 155689-45-5 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1994,vol. 59,p. 195 - 202

29
[ 1138-80-3 ]
[ 92398-47-5 ]
[ 90058-40-5 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1993,vol. 58,p. 2987 - 2993

30
[ 1738-86-9 ]
[ 56-40-6 ]
[ 100-02-7 ]
[ 2566-19-0 ]
[ 1138-80-3 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1987,vol. 23,p. 1583 - 1588
Zhurnal Organicheskoi Khimii,1987,vol. 23,p. 1775 - 1781

31
dibenzyl pyrocarbonate [ No CAS ]
[ 56-40-6 ]
[ 2566-19-0 ]
[ 1138-80-3 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 5375 - 5376

32
[ 90-34-6 ]
[ 1138-80-3 ]
[4-(6-Methoxy-quinolin-8-ylamino)-pentylcarbamoyl]-methyl}-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1994,vol. 33,p. 251 - 254

33
[ 27781-44-8 ]
[ 6945-92-2 ]
[ 1138-80-3 ]
[ 3842-37-3 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1962,vol. 17,p. 263 - 272

34
[ 67-56-1 ]
[ 7535-72-0 ]
[ 17331-93-0 ]
[ 1421-69-8 ]
[ 1212-53-9 ]
[ 1138-80-3 ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 2343 - 2346

35
[ 67-56-1 ]
[ 7535-72-0 ]
[ 1421-69-8 ]
[ 1212-53-9 ]
[ 1138-80-3 ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 2343 - 2346

36
[ 7535-72-0 ]
[ 17331-93-0 ]
[ 1421-69-8 ]
[ 1212-53-9 ]
[ 1138-80-3 ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 2343 - 2346

37
[ 7535-72-0 ]
[ 1421-69-8 ]
[ 1212-53-9 ]
[ 1138-80-3 ]

Reference： [1]Tetrahedron Letters,1995,vol. 36,p. 2343 - 2346

38
[ 1145-81-9 ]
[ 1138-80-3 ]

Yield	Reaction Conditions	Operation in experiment
	With water; potassium carbonate; In ethanol;Heating / reflux;	The residue obtained in the above step, which had been dissolved in 250 ml of ethanol, was treated with 10% potassium carbonate solution and heated under reflux overnight. The ethanol was evaporated, and the aqueous phase was acidified (pH=1) with concentrated HCl. The precipitate obtained was filtered and dried to produce 105 g of a white solid. Yield: 90%. Melting point: 110 C. Rf: 0.25 (CH2Cl2/MeOH, 90:10 v/v). IR (KBr): 1678 (CC), 1727(OCO) cm-1 1H NMR (200 MHz, CDCl3, HMDS) delta ppm: 7.24 (m, 5H, Har), 5.23 (s1, 1H, NH), 5.06 (s, 2H, CH2, PhCH2), 4.63 (s, 1H, OH), 3.94 (d, 2H, J=5.50 Hz, CH2COOH).

Reference： [1]Synthetic Communications,1995,vol. 25,p. 553 - 559
[2]Patent: US2005/75345,2005,A1 .Location in patent: Page/Page column 10

39
[ 67-56-1 ]
[ 1138-80-3 ]
[ 1212-53-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride; at 0℃; for 2h;Inert atmosphere;	A 300-mL three-necked round-bottomed flask equipped with a magnetic stirring bar and fitted with a dropping funnel was charged with N-Cbz-glycine (2.50g, 12.0mmol) and methanol (60mL). The flask was cooled to 0°C, and thionyl chloride (1.20mL, 16.5mmol, 1.4equiv) was added to the vigorously stirred solution over a period of 10min. The mixture was stirred for additional 2h, after which time TLC (ethyl acetate) indicated complete consumption of the starting N-Cbz-glycine. The reaction mixture was concentrated under reduced pressure to give a crude material, which was purified by silica gel column chromatography (ethyl acetate) to afford N-Cbz-glycine methyl ester (2.66g, 11.9mmol, 99percent) as a colorless oil. Rf=0.55 (ethyl acetate). 1H NMR (400MHz, CDCl3): delta 7.32?7.18 (m, 5H), 5.58 (br s, 1H), 5.02 (s, 2H), 3.84 (d, 2H, J=5.6Hz), 3.62 (s, 3H). 13C NMR (100MHz, CDCl3): delta 170.4, 156.2, 136.1, 128.2, 127.9, 127.8, 66.7, 51.9, 42.3. IR (neat, cm?1): 3337, 2953, 1701, 1508, 1443, 1364, 1207, 1051, 1004. HRMS-EI calcd for C11H13NO4 (M+) 223.0845; found 223.0833.

Reference： [1]Chemical Communications,2010,vol. 46,p. 2641 - 2643
[2]Tetrahedron,2013,vol. 69,p. 10946 - 10954
[3]Journal of Organic Chemistry,1995,vol. 60,p. 7072 - 7074
[4]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 225 - 235
[5]Heterocycles,2008,vol. 75,p. 2477 - 2491
[6]Applied Organometallic Chemistry,2015,vol. 29,p. 661 - 667

40
[ 10466-56-5 ]
[ 1138-80-3 ]
[((1S,2S)-1-Carbamoyl-2-methyl-butylcarbamoyl)-methyl]-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2030 - 2039

41
[ 1212-53-9 ]
[ 1138-80-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1623 - 1627

42
[ 72784-43-1 ]
[ 1138-80-3 ]
[ 191033-44-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1997,vol. 62,p. 941 - 947

43
[ 7647-01-0 ]
[ 1138-80-3 ]
[ 1145-81-9 ]
[ 623-33-6 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 951,956

44
[ 2566-19-0 ]
papain-substances [ No CAS ]
[ 1138-80-3 ]
[ 56-40-6 ]

Reference： [1]Journal of Biological Chemistry,1935,vol. 111,p. 225,243
Journal of Biological Chemistry,1936,vol. 115,p. 593,596, 599

45
[ 2836-03-5 ]
[ 1138-80-3 ]
[ 696605-19-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 876 - 883

46
[ 5259-97-2 ]
[ 1138-80-3 ]
3-(Z-glycyl)oxazinan-2-one [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 3309 - 3313

47
[ 1138-80-3 ]
[ 115761-79-0 ]
[ 946522-89-0 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3706 - 3715

48
[ 1138-80-3 ]
[ 170161-27-0 ]
[ 957829-77-5 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 8280 - 8289

49
[ 1138-80-3 ]
[ 1160-54-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 501 - 517
[2]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 3253 - 3260
[3]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 584 - 589
[4]Chemistry - A European Journal,2012,vol. 18,p. 2632 - 2638

50
[ 1138-80-3 ]
polymer supported Meldrum's acid [ No CAS ]
[ 105258-93-3 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 1536 - 1547

51
[ 1138-80-3 ]
[ 105258-93-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2277 - 2280

52
[ 1138-80-3 ]
L-thiophenylalanine-<4-nitro-phenyl ester> [ No CAS ]
[ 1160-54-9 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 3039 - 3042

53
[ 1138-80-3 ]
[ 1212-53-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1964,vol. 83,p. 345 - 363

54
[ 1138-80-3 ]
[ 1145-81-9 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1964,vol. 83,p. 345 - 363

55
exo-3-aminotropane [ No CAS ]
[ 1892-57-5 ]
[ 1138-80-3 ]
benzyl exo-3-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino]-2-oxoethylcarbamate [ No CAS ]

Reference： [1]Patent: EP1213289,2002,A1 .Location in patent: Page 13

56
[ 766545-20-4 ]
[ 1138-80-3 ]
C₁₈H₁₈ClN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 0℃; for 2h;	A solution of 90 mg of <strong>[766545-20-4]2-chloro-5,6,7,8-tetrahydro-[1,6]naphthyridine hydrochloride</strong> (U.S. Pat. No. 6,169,093), 0.134 g of N-carbobenzyloxyglycine, 0.130 g of triethylamine, and 0.087 g of 1-hydroxy-7-azabenzotriazole in DMF (2.7 mL) at 0 C. was stirred as 0.123 g (0.640 mmol) of EDC was added. After two hrs., the reaction mixture was poured into 4% magnesium sulfate solution, and the resulting solution was extracted with EtOAc and then methylene chloride. The organic extracts were dried over sodium sulfate, filtered, and concentrated to give an oil that solidified upon standing. Trituration with MeOH and collection of the solids provided the desired amide intermediate.
	With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 0℃; for 2h;	Preparation 26 2-Amino-1-(7w8-dihydro-5H-r1, 61naphthvridin-6-yl)-ethanone; Step A A solution of 90 mg of 2-chloro-5, 6,7, 8-tetrahydro- [1, 6] naphthyridine hydrochloride (U. S. Pat. No. 6,169, 093), 0.134 g of N-carbobenzyloxyglycine, 0.130 g of triethylamine, and 0.087 g of 1-hydroxy-7-azabenzotriazole in DMF (2.7 mL) at 0 C was stirred as 0.123 g (0.640 mmol) of EDC was added. After two h, the reaction mixture was poured into 4% magnesium sulfate solution, and the resulting solution was extracted with EtOAc and then methylene chloride. The organic extracts were dried over sodium sulfate, filtered, and concentrated to give an oil that solidified upon standing. Trituration with MeOH and collection of the solids provided the desired amide intermediate.

Reference： [1]Patent: US2004/192698,2004,A1 .Location in patent: Page/Page column 13
[2]Patent: WO2005/35532,2005,A1 .Location in patent: Page/Page column 29-30

57
[ 344-80-9 ]
[ 1138-80-3 ]
Benzyl[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]methyl}-carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; sodium hydrogencarbonate; In tetrahydrofuran; ethyl acetate;	(a) 45 g of carbobenzoxy-glycine dissolved in 1 liter of absolute tetrahydrofuran are treated dropwise while cooling with ice with 20 ml of thionyl chloride and stirred for 1 hour while cooling with ice. There is then rapidly added dropwise thereto a suspension of 50 g of <strong>[344-80-9]2-amino-5-nitro-2'-fluorobenzophenone</strong> in 200 ml of absolute tetrahydrofuran and the mixture is stirred at room temperature for 18 hours. The solution obtained is concentrated and the residue is treated with ice and 10% sodium bicarbonate solution and extracted with methylene chloride. The organic solution is dried over sodium sulphate, filtered and concentrated. The residue is dissolved in a small amount of hot ethyl acetate, concentrated partially and treated with ether. Benzyl[[2-(o-fluorobenzoyl)-4-nitrophenyl]carbamoyl]methyl}-carbamate is obtained. The mother liquors are purified on a 100 g silica gel column using methylene chloride as the eluding agent, an additional amount of the aforementioned product being obtained.

Reference： [1]Patent: US4251443,1981,A

58
Z-Gly-ONB [ No CAS ]
[ 1138-80-3 ]
[ 56-40-6 ]
[ 2566-19-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In tetrahydrofuran; water;	EXAMPLE 22 Production of Z-Gly-Gly-OH In 100 ml of water were dissolved under heating 15 g of Gly and 16.8 g of sodium hydrogencarbonate. The solution was cooled with ice. To the solution was added a solution of Z-Gly-ONB (prepared using 40 g of Z-Gly-OH) in 400 ml of THF under ice-cooling, followed by stirring for 40 hours. The resulting THF was distilled off and the solution was acidified with hydrochloric acid. Crystals were recovered by filtration and washed with water. Yield 44.4 g (87.3%); m.p. 169-172 C.; Rf1 =0.21 Elemental analysis, for C12 H14 O5 N2: Calcd.: C, 54.13; H, 5.30; N, 10.52; Found: C, 53.78; H, 5.10; N, 10.25

Reference： [1]Patent: US4358440,1982,A

59
[ 1138-80-3 ]
[ 39608-31-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylsilane; toluene-4-sulfonic acid; trifluoroacetic acid; paraformaldehyde; In chloroform; benzene;	EXAMPLE 3 A mixture of Cbz-glycine (10.46 g, 50 mmoles), paraformaldehyde (0.066 equiv.), and p-toluenesulfonic acid (500 mg) in benzene (400 ml) was refluxed for 30 min. with azeotropic water removal. The solution was cooled and washed with 1N aqueous NaHCO3 (2*100 ml) and dried over Na2 SO4. Concentration in vacuo gave a crystalline solid. Recrystallization from benzene-low boiling petroleum ether gave 5.84 g (53%) of product, mp 79-80 (lit. mp. 84, D. Ben-Ishai, J. Amer. Chem. Soc., 79, 5736 (1957)). The oxazolidinone from Cbz-glycine (221 mg, 1.0 mmole) was dissolved in 10 ml of CHCl3 and triethylsilane (193 l=174 mg, 1.5 mmoles) and trifluoroacetic acid (770 mul, 10 mmoles) were added. The solution was stirred at room temperature for 2 hrs. and concentrated in vacuo. CHCl3 was added and the solution was reconcentrated to a colorless oil. Silica gel chromatography gave 107 mg (48%) of Cbz-sarcosine, identified by NMR (N-Me, 2.98 ppm) and amino acid analysis.

Reference： [1]Patent: US4535167,1985,A

60
[ 1138-80-3 ]
[ 1022-13-5 ]
[ 60067-08-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With phosphorus pentachloride; hydrogen bromide; potassium hydrogencarbonate; In chloroform; water; acetic acid;	b. 84 g. of N-benzyloxycarbonylglycine were suspended in 500 ml. of alcohol-free chloroform and the suspension was cooled to -20° C. The stirred suspension was treated portionwise over a period of 15 minutes with 90 g. of phosphorus pentachloride and the stirring was continued until a clear solution was obtained. At this point, the cold mixture was added dropwise over a period of 30 minutes to a cold (-5° C.) vigorously stirred emulsion consisting of 82 g. of 5-chloro-2-methyl-aminobenzophenone, 347 g. of potassium bicarbonate, 700 ml. of chloroform and 1400 ml. of water. The resulting mixture was stirred for a further 1 hour at -5° C. and then overnight at room temperature. The stirring was then discontinued and the liquid phases allowed to separate. The chloroform layer was washed three times with 500 ml. of water each time and evaporated in vacuo to give 150.7 g. of a viscous yellow gum which was shown by physical methods to be almost pure (above 95percent) 2-(N-benzyloxycarbonylamino)-N-(2-benzoyl-4 -chlorophenyl)-N-methylacetamide. The product obtained according to the preceding paragraph was dissolved in 650 ml of a 30percent solution of hydrogen bromide in glacial acetic acid and treated in an identical manner to that described in part (a) of this Example to give 2-amino-N-(2-benzoyl-4-chlorophenyl)-N-methylacetamide hydrobromide in a 77percent overall yield from 5-chloro-2-methylaminobenzophenone.

Reference： [1]Patent: US4007219,1977,A

61
2-ethoxycarbonyloxyimino-2-cyanoacetic acid amide [ No CAS ]
[ 1138-80-3 ]
[ 1145-81-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; ethyl acetate;	EXAMPLE F To a solution of N-benzyloxycarbonylglycine (1.05 g) and triethylamine (0.73 ml) in ethyl acetate (10 ml) and tetrahydrofuran (10 ml), 2-ethoxycarbonyloxyimino-2-cyanoacetic acid amide (1.11 g) is added, and the resulting mixture is stirred for 2 hours. The reaction mixture is treated as in Example A to give N-benzyloxycarbonylglycine ethyl ester (1.2 g) as an oil. IR absorption spectrum: 3550 cm-1 (NH); 1730 cm-1 (C=O of ester)
	With triethylamine; In N-methyl-acetamide;	EXAMPLE G To a solution of N-benzyloxycarbonylglycine (1.05 g) and triethylamine (0.73 ml) in dimethylformamide (9 ml), 2-ethoxycarbonyloxyimino-2-cyanoacetic acid amide (1.11 g) is added, and the resulting mixture is stirred for 2 hours. The reaction mixture is treated as in Example A to give N-benzyloxycarbonylglycine ethyl ester (0.2 g) as an oil.

Reference： [1]Patent: US3976635,1976,A
[2]Patent: US3976635,1976,A

62
2-methoxycarbonyloxyimino-2-cyanoacetic acid amide [ No CAS ]
[ 1138-80-3 ]
[ 1212-53-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In chloroform; acetonitrile;	EXAMPLE I To a solution of N-benzyloxycarbonylglycine (1.05 g) and triethylamine (0.7 ml) in chloroform (10 ml) and acetonitrile (5 ml), 2-methoxycarbonyloxyimino-2-cyanoacetic acid amide (0.85 g) is added, and the resulting mixture is stirred at room temperature for 1 hour and allowed to stand over night. The reaction mixture is treated as in Example A to give N-benzyloxycarbonylglycine methyl ester (1.1 g) as an oil. Mass spectrum: M+ = 223 IR absorption spectrum: 3350 cm-1 (NH); 1740 - 1710 cm-1 (C=O of ester and C=O of urethane)

Reference： [1]Patent: US3976635,1976,A

63
C₁₈H₁₇N₂O₃Pol [ No CAS ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 85157-21-7 ]
[ 1138-80-3 ]
[ 1135458-88-6 ]

Reference： [1]Chemical Communications,2009,p. 671 - 673

64
[ 117921-54-7 ]
[ 1138-80-3 ]
C₁₆H₁₉N₃O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6672 - 6684

65
[ 6089-09-4 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 85157-21-7 ]
[ 1138-80-3 ]
[ 204777-78-6 ]
[ 1201896-27-6 ]

Reference： [1]Chemical Communications,2009,p. 6601 - 6603

66
[ 1138-80-3 ]
[ 74-88-4 ]
[ 1212-53-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃; for 46h;Inert atmosphere;	To a stirred solution of Cbz-glycine (1, 2.56 mmol, 0.54 g) in DMF (3.0 mL) wasadded sodium bicarbonate (3.38 mmol, 0,28 g) followed by methyl iodide (9.64mmol, 0.60 mL). The mixture was stirred under nitrogen atmosphere for 46 h atroom temperature. After this time, 30 mL of ethyl acetate was added and themixture was washed with distilled water (three times). The organic phase wasseparated, dried with sodium sulfate and concentrated to yield product 2 (2.38mmol, 0.53 g, 93percent yield), which was used without further purification.Compound 3a was prepared following the general procedure for the preparationof hydrazide (refluxing for 3 h) using product 2 (4.93 mmol, 1.10 g), hydrazinehydrate (17.2 mmol, 0.86 g) and 1.4 mL of ethanol. Purification by columnchromatography (CH2Cl2 ? 10percent MeOH/CH2Cl2) furnished 3a in 69percent yield(0.76 g, 3.42 mmol) as a white solid.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2865 - 2872
[2]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 2596 - 2602
[3]Journal of Combinatorial Chemistry,2010,vol. 12,p. 248 - 254

67
[ 26081-03-8 ]
[ 1138-80-3 ]
[ 449797-38-0 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 3779 - 3781

68
[ 931-53-3 ]
[ 1138-80-3 ]
[ 25055-82-7 ]
[ 1255731-88-4 ]

Reference： [1]Synthesis,2010,p. 2997 - 3003

69
[ 1138-80-3 ]
[ 61985-23-7 ]
[ 1212-53-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	In acetonitrile; at 80℃; for 24h;Inert atmosphere; Sealed vial;	General procedure: Carboxylic acid (0.5 mmol) and MImC (2a, 1.0 mmol) were placed in a dry 20 mL vial with a Teflon tape-coated thread. A magnetic stirbar was added, followed by dry MeCN (1.0 mL), and the vial was quickly sealed with a plastic cap (gas is evolved during the course of the reaction. All experiments should be performed behind a blast shield if a sealed container is used.). The reaction mixture was then stirred at 23 °C for 15 min and then heated to 80 °C using a heating block for 24 h. The mixture was cooled to room temperature and then the vial was carefully opened (CAUTION: vial under pressure.). The volatiles were removed in vacuo, the resulting residue was dissolved in diethyl ether (20 mL), and then washed with 1 M HCl (10 mL). The aqueous layer was back-extracted with diethyl ether (20 mL) and the organic fractions were combined, washed with a saturated solution of NaHCO3 and then brine, dried over MgSO4, and concentrated in vacuo to afford the desired ester.

Reference： [1]Organic Letters,2010,vol. 12,p. 4572 - 4575
[2]Tetrahedron,2011,vol. 67,p. 8851 - 8859

70
[ 19213-72-0 ]
[ 1138-80-3 ]
[ 1145-81-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	In acetonitrile; at 80℃; for 24h;Inert atmosphere; Sealed vial;	General procedure: Carboxylic acid (0.5 mmol) and MImC (2a, 1.0 mmol) were placed in a dry 20 mL vial with a Teflon tape-coated thread. A magnetic stirbar was added, followed by dry MeCN (1.0 mL), and the vial was quickly sealed with a plastic cap (gas is evolved during the course of the reaction. All experiments should be performed behind a blast shield if a sealed container is used.). The reaction mixture was then stirred at 23 C for 15 min and then heated to 80 C using a heating block for 24 h. The mixture was cooled to room temperature and then the vial was carefully opened (CAUTION: vial under pressure.). The volatiles were removed in vacuo, the resulting residue was dissolved in diethyl ether (20 mL), and then washed with 1 M HCl (10 mL). The aqueous layer was back-extracted with diethyl ether (20 mL) and the organic fractions were combined, washed with a saturated solution of NaHCO3 and then brine, dried over MgSO4, and concentrated in vacuo to afford the desired ester.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8851 - 8859

71
[ 373-88-6 ]
[ 1138-80-3 ]
[ 1371632-79-9 ]

Yield	Reaction Conditions	Operation in experiment
78%		N,N-Carbonyldiimidazole (38.72 g, 0.2328 mol) was added to a slurry ofN-[(phenylmethoxy)carbonyl]glycine (50 g, 0.239 mol) in ethyl acetate (350 mL) over 5 mins. The resulting solution was stirred for 65 minutes, then trifluoroethylamine hydrochloride (32.9 g, 0.24 mol) was added in portions keeping the temperature at 22 C. The reaction mixture was stirred for 17 hrs, then quenched with water (250 mL) and extracted with ethyl acetate (150 mL). The resulting biphasic mixture was allowed to settle and the phases were separated. The organic phase was washed twice with 1 Nu hydrochloric acid (100 mL each) and dried over magnesium sulfate (20 g) overnight. The slurry was filtered and the residue washed with 4 portions of ethyl acetate (50 mL, 100 mL, 100 mL, 50 mL). The washes and the filtrate were combined and concentrated to a solid. The solid was dried in a vacuum oven at 40 C to give the title compound as a white solid (54.1 g, 78% yield).1H NMR (DMSO-d6): 8.55 (tr, / = 6.4 Hz, 1H), 7.53 (tr, J= 6.1 Hz, 1H), 7.43 - 7.22 (m, 5H), 5.04 (s, 2H), 4.01-3.79 (m, 2H), 3.68 ppm (d, J = 6.1 Hz ,2 H); 19F-NMR (DMSO-d6): - 70.76 ppm (tr, / = 10.1Hz).

Reference： [1]Patent: WO2012/47543,2012,A1 .Location in patent: Page/Page column 13; 28

72
[ 5241-58-7 ]
[ 1212-53-9 ]
[ 5513-69-9 ]
[ 1138-80-3 ]

Reference： [1]ChemBioChem,2012,vol. 13,p. 1319 - 1326

73
C₂₁H₂₆N₃O₅Pol [ No CAS ]
azido-4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-1-O-trifuoro-N-phenylimidate-D-galactopyranoside [ No CAS ]
[ 123639-61-2 ]
[ 71989-35-0 ]
[ 1138-80-3 ]
[ 507-09-5 ]
[ 55722-49-1 ]
C₇₄H₉₅N₇O₂₇ [ No CAS ]
C₇₄H₉₅N₇O₂₇ [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1851 - 1853

74
[ 27514-07-4 ]
[ 1138-80-3 ]
[ 1622401-46-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20℃; for 3.16h;	To a stirred solution of ((benzyloxy)carbonyl)glycine (0.80, 3.8 mmol) in 25 mL of dichloromethane at rt,HATU (1.60 g, 4.2 mmol) and DIPEA (1.5 g, 11.6 mmol) were added. The reaction mixture was stirred for 10 mm, and then 7-azabicyclo[2.2. 1]heptane hydrochloride (0.76 g, 5.7 mmol) was added, and stirred for another 3 h. The resulting reaction mixture was filtered and the filtrate was concentrated. The obtained residue was purified by flash column chromatography (EtOAc/hexane, 8:2) to obtain 1 g (91 %) of benzyl(2-(7-azabicyclo[2.2.1]heptan-7-yl)-2-oxoethyl)carbamate as a clear oil.

Reference： [1]Patent: WO2014/127315,2014,A1 .Location in patent: Page/Page column 57

75
[ 1138-80-3 ]
[ 192130-34-0 ]
tert-butyl 4-(2-(2-(((benzyloxy)carbonyl)amino)acetamido)ethyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]MedChemComm,2014,vol. 5,p. 1892 - 1898

76
[ 5497-76-7 ]
[ 1138-80-3 ]
[ 24277-16-5 ]

Yield	Reaction Conditions	Operation in experiment
1.45 g		Step a) Synthesis of Z-Gly-Pro tert-Butyl EsterA solution of Z-Gly (1 .087 g, 5.2 mmol), and N-methylmorpholine (0.571 mL, 5.2 mmol) in THF (15mL), was cooled to -15C, and treated with isobutyl chloroformate (0.679 mL, 5.2 mmol). After stirring for 10 min at -15C, the mixture was treated with L-proline t-butyl ester-HCI (0.831 g, 4.0 mmol), and N- methylmorpholine (0.571 mL, 5.2 mmol). Work-up: the reaction mixture was diluted with ethyl acetate (50 mL), washed with 1 N HCL, 1 N NaHC03, and brine, then dried with anhydrous Na2S04. This solution was filtered and concentrated to give 1 .45 g of a white solid. This material was used in the next step without further purification.

Reference： [1]Patent: WO2015/164289,2015,A1 .Location in patent: Page/Page column 65

77
[ 1190307-88-0 ]
[ 1138-80-3 ]
C₃₂H₃₈FN₄O₁₂P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.1%		The Cbz-Gly-OH (209mg, 1mmol) with 2mlN, N- dimethylformamide (DMF) was dissolved, cooled to -5 deg. C, added with stirringThe DIC (63.1mg, 0.5mmol), at room temperature for 30min, continued to cool to -5 deg C , followed by adding S1 in (265mg, 0.5mmol)2mlDMF , then added triethylamine (60.7mg, 0.6mmol), and a catalytic amount of 4-dimethylaminopyridine (of DMAP), were added at room temperature for 4h.Completion of the reaction was poured into 10ml water, extracted with 10ml ethyl acetate 3 times, the organic layers combined, dried over anhydrous sodium sulfate, the solvent spin dry,Yellow solid, purified by silica gel column chromatography, to obtain white powder (M1) 217mg, 60.1% yield.

Reference： [1]Patent: CN105254695,2016,A .Location in patent: Paragraph 0044; 0045; 0046

78
[ 75680-92-1 ]
[ 1138-80-3 ]
ethyl 5-((benzyloxycarbonylamino)methyl)-6-chloropyridazine-3-carboxylate [ No CAS ]

Reference： [1]ACS Combinatorial Science,2016,vol. 18,p. 651 - 654

79
[ 75-44-5 ]
5-hydroxy-2-nitrophenethyl alcohol [ No CAS ]
[ 53844-02-3 ]
[ 1138-80-3 ]
C₁₂H₉N₃O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1.7 g 5-hydroxy-2-nitrophenethyl alcohol and 4.3 g potassium carbonate were dispersed in 20 ml of N,N'-dimethylformamide. Heat to 60 C and stir for 1 hour. Slowly add dropwise 2.82 g <strong>[53844-02-3]N-benzyloxycarbonyl-2-bromoethylamine</strong> in dichloromethane solution (5 ml). At 60 C react for 24 hours. After the reaction, to remove the solvent under reduced pressure, ethyl acetate to dissolve the product is used, with saturated sodium bicarbonate solution, washed with saturated sodium chloride solution and the two, a water washing of the distillation, the organic phase with anhydrous magnesium sulfate drying 8 hours, filtered and concentrated by decompression, the recrystallization in ethyl acetate/cyclohexane two, to obtain the product A.1.56 g product A was dissolved in 50 ml anhydrous dichloromethane. Under ice-bath cooling, add 0.96 g N-benzyloxycarbonylglycine, 1.33 g N,N'-dicyclohexyl-carbodiimide and 0.2 g 4-dimethylaminopyridine. Stir the mixture at room temperature for overnight. After the reaction is ended, with the freezing dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution the two washing, a water washing of the distillation, drying by anhydrous sodium sulfate overnight. Filtering and vacuum to remove the solvent, the two re-crystallization in ethyl acetate. The obtained crystal is dissolved in 20 ml of chloroform, added under ice bath 20 ml of ethyl acetate saturated solution of hydrogen chloride, the reaction at room temperature 4 hours after drying under reduced pressure, to obtain the product B.0.54 g product B was dissolved in 50 ml methylene chloride and 8 ml pyridine mixed solvent. Cool to -20 C. Add dropwise 10 ml toluene solution of phosgene (1.93 mole per liter). React for 6 hours. The reaction solution with dilute hydrochloric acid and saturated sodium bicarbonate solution wash two times the, saturated sodium chloride solution and distilled water once the washing. The organic phase with anhydrous magnesium sulfate drying sleepovers, filtered concentrated under reduced pressure.

Reference： [1]Patent: CN105601549,2016,A .Location in patent: Paragraph 0056; 0057; 0058; 0059; 0060; 0061

80
[ 64-17-5 ]
[ 108849-83-8 ]
[ 1145-81-9 ]
[ 4180-62-5 ]
[ 1138-80-3 ]
Z-Gly-Ser-OEt [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 3311 - 3314

81
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 132327-80-1 ]
[ 132684-59-4 ]
[ 1138-80-3 ]
2-chlorotrityl resin [ No CAS ]
Cbz-GPIQ(Trt)-E(tBu)-hPhe-L-OH [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4496 - 4502

82
[ 1138-80-3 ]
[ 68-12-2 ]
[ 1857-19-8 ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 1765 - 1773

83
[ 1138-80-3 ]
[ 2673-19-0 ]
(S)-4-t-butyl 1-methyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; at 0 - 20℃; for 16.5h;	N-Carbobenzoxyglycine (Z-Gly-OH) (11.48 g, 54.8 mmol)And L-aspartic acid 4-t-butyl-1-methyl ester hydrochloride (13.14 g, 54.8 mmol) were dissolved in tetrahydrofuran (275 ml) 1-Hydroxybenzotriazole hydrate (HOBt) (8.90 g, 65.8 mmol) and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC.HCl) (11.31 g, 65.8 mmol) was added and triethylamine (23.1 mL, 164.6 mmol) was added dropwise. The reaction mixture was further stirred at 0 C for 30 minutes and then at room temperature for 16 hours. After completion of the reaction, water (200 mL) was added to the reaction mixture, and the mixture was washed three times with ethyl acetate (100 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (200 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure The residue was separated and purified by column chromatography to obtain (S) -4-t-butyl 1-methyl 2- (2- (((benzyloxy) carbonyl) amino) acetamido) succinate (16.0 g, 74% Was obtained

Reference： [1]Patent: KR2017/133845,2017,A .Location in patent: Paragraph 0078; 0080

84
[ 1138-80-3 ]
[ 172876-96-9 ]
benzyl 2,4-dioxoimidazolidine-1-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 524 - 528

85
[ 1138-80-3 ]
[ 711007-44-2 ]
benzyl ((4-carbamoyl-1H-benzo[d]imidazol-2-yl)methylene)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Cbz-glycine (2.92 g, 13.89 mmol) and 120 mL of acetonitrile were added to a 250 mL reaction flask, stirred and dissolved, and CDI (2.57 g, 15.85 mmol) was slowly added, and reacted at 45 C for 1.5 hours.TLC (dichloromethane: methanol = 10:1) to monitor the reverse of the raw materialsAfter completion, Intermediate VII (2 g, 13.23 mmol) was added and the mixture was reacted at 45 C for 4 hours.The reaction of the starting material was monitored by TLC (dichloromethane:methanol = 10:1) to yield a large white solid which was filtered and dried.Add it to a 100 mL reaction flask, add 50 mL of glacial acetic acid, and reflux at 120 C.TLC (dichloromethane:methanol = 10:1) was used to monitor the starting material. After concentrating under reduced pressure, glacial acetic acid was removed and dissolved in 100 mL of water.The organic layer was combined and washed with saturated sodium chloride (150 mL). Filtering,The filtrate was concentrated to give a crude material (VIII), 4.18 g, yield 97.4%.
		Cbz-glycine (2.92 g, 13.89 mmol) and 120 mL of acetonitrile were added to a 250 mL reaction flask, stirred and dissolved, and CDI (2.57 g, 15.85 mmol) was slowly added, and reacted at 45 C for 1.5 hours. After the reaction of the material was monitored by TLC (dichloromethane:methanol = 10:1), Intermediate VII (2 g, 13.23 mmol) was added and reacted at 45 C for 4 hours. TLC (dichloromethane: methanol = 10:1) monitoringAfter the raw materials are reacted, a large amount of white solid is produced, suction filtered, and dried. It was added to a 100 mL reaction flask, 50 mL of glacial acetic acid was added, and the reaction was refluxed at 120 C. After the reaction of the material was monitored by TLC (dichloromethane:methanol = 10:1), the glacial acetic acid was concentrated under reduced pressure and dissolved in 100 mL of water.Extracted with ethyl acetate (100 mL × 2), and the organic layer was combined.Wash with saturated sodium chloride (150 mL) and dry over anhydrous sodium sulfate. Filtered off with suction, the filtrate was concentrated to give the crude product (VIII) 4.18g, yield 97.4%.

Reference： [1]Patent: CN109251204,2019,A .Location in patent: Paragraph 0076; 0080; 0081
[2]Patent: CN109748923,2019,A .Location in patent: Paragraph 0090; 0094-0095

86
[ 153-78-6 ]
[ 1138-80-3 ]
<i>N</i>-benzyloxycarbonyl-glycine fluoren-2-ylamide [ No CAS ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,2019,vol. 194,p. 540 - 544

87
[ 73368-41-9 ]
[ 1138-80-3 ]
ethyl 4-(2-(((benzyloxy)carbonyl)amino)acetamido)-3-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; at 0 - 20℃; for 12.0h;Inert atmosphere;	To a mixture of 2-(benzyloxycarbonylamino)acetic acid (5. 9 g, 28.17 mmol, 1.1 eq) and ethyl 4-amino-3-methoxy-benzoate (5 g, 25.61 mmol, 1 eq) in tetrahydrofuran (50 mL) was added 0-(7-azabenzotriazol-l-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (11.7 g, 30.74 mmol, 1.2 eq) and N,N-diisopropylethylamine (6.6 g, 51.23 mmol, 8.9 mL, 2 eq) at 0 C under nitrogen. The mixture was warmed to 20 C and stirred for 12 hours. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL x 3). The combined organic phase was washed with brine (200 mL x 2), dried with anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate = 10/1, 3/1 to 1/1) to give ethyl 4-[[2-(benzyloxycarbonylamino)acetyl]amino]-3-methoxy-benzoate (9 g, 23.29 mmol, 91% yield) as a yellow oil. 1H-NMR (400MHz, CDCb) d 8.41 (br d, J = 8.4 Hz, 2H), 7.68 (br d, J = 8.4 Hz, 1H), 7.53 (s, 1H), 7.42 - 7.28 (m, 5H), 5.61 (br s, 1H), 5.18 (s, 2H), 4.42 - 4.32 (m, 2H), 4.11 - 4.01 (m, 2H), 3.88 (s, 3H), 1.40 (t, J = 1.2 Hz, 3H).

Reference： [1]Patent: WO2019/195609,2019,A2 .Location in patent: Paragraph 00671-00672

88
[ 55276-43-2 ]
[ 1138-80-3 ]
C₁₅H₂₁N₃O₅S [ No CAS ]

Reference： [1]Molecular Cancer Therapeutics,2019,vol. 18,p. 1973 - 1984

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[ CAS No. 1138-80-3 ] {[proInfo.proName]}

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[ 1138-80-3 ] Synthesis Path-Upstream 1~15

[ 1138-80-3 ] Synthesis Path-Downstream 1~88

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Amino Acid Derivatives

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