Boc-DL-Ala-OH | tert-Butoxycarbonyl-DL-alanine | N-protective Amino Acid

Boc-DL-Ala-OH is a protected alanine derivative with the amino group protected by tert-butoxycarbonyl (Boc), having both D and L configurations, suitable for peptide synthesis.

Synonyms: tert-Butoxycarbonyl-DL-alanine

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Quality Control of Boc-DL-Ala-OH Purity: 95% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of Boc-DL-Ala-OH

CAS No. :	3744-87-4
Formula :	C₈H₁₅NO₄
M.W :	189.21
SMILES Code :	CC(OC(NC(C(O)=O)C)=O)(C)C
Synonyms :	tert-Butoxycarbonyl-DL-alanine
MDL No. :	MFCD00063124
InChI Key :	QVHJQCGUWFKTSE-UHFFFAOYSA-N
Pubchem ID :	268471

Safety of Boc-DL-Ala-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of Boc-DL-Ala-OH

* 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.

Downstream synthetic route of [ 3744-87-4 ]

[ 3744-87-4 ] Synthesis Path-Downstream 1~22

1
[ 6066-82-6 ]
[ 3744-87-4 ]
[ 34404-33-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide; at 0℃;	General procedure: The general scheme for the synthesis of AA-CAMderivatives is shown in Fig. S1 and the details ofchemical synthesis are provided in the SupplementaryMethods section. CAM [(1R,2R)-2-amino-1-(4--nitrophenyl)propane-1,3-diol)] was prepared asdescribed previously [23]. Amino acids with protectedalpha- and side-chain amino groups wereactivated by reaction with N-hydroxysuccinimide inthe presence of N,N?-dicyclohexylcarbodiimide at0 C. The resulting succinimide-reactive esters wereused for the acylation of CAM in the presence ofdiisopropylethylamine as a base at room temperature.Subsequent deprotection was achieved bytreatment of the obtained amino-acid CAM derivativeswith trifluoroacetic acid and appropriate scavengers.Synthesized AA-CAM derivatives were purifiedby columnchromatography on silica gel using suitablesystems of solvents. For generating N-acetylatedvariants of AA-CAM, additional acetylation wasperformed by reacting the unprotected AA-CAMderivatives with the N-acetylsuccinimide. Purity andchemical structures of obtained compounds wereconfirmed by HPLC, LC-MS, and NMR spectroscopy(see Supplementary Methods).

References: [1]Journal of the Chemical Society. Chemical communications,1987,p. 1155 - 1156.
[2]Journal of the American Chemical Society,1996,vol. 118,p. 6975 - 6985.
[3]Journal of Molecular Biology,2018,vol. 430,p. 842 - 852.

2
[ 3744-87-4 ]
[ 74-88-4 ]
[ 91103-47-8 ]

Yield	Reaction Conditions	Operation in experiment
96%		Intermediate 57 Boc-D-AlaOMe Boc-D-AlaOH (10.0 g, 52.9 mmol) was dissolved in dry DMF (60 mL), then potassium carbonate (8.0 g, 58.0 mmol) was added, the mixture was stirred at rt for 15 min, and methyl iodide (6.58 mL, 106.0 mmol) was added dropwise. The stirring was maintained for 18h. Then, the mixture was concentrated in vacuo and the residue was dissolved in EtOAc (lOOmL). The organic layer was washed with water, brine, dried over MgSCU, filtered and concentrated. The crude product was purified by flash column chromatography (silica gel, DCM/MeOH 0 to 1%) to give 10.36 g (51.0 mmol, 96% yield) of the title compound. *Eta NMR (DMSO-d6) delta 7.46 (1H, d), 4.35 (1H, m), 3.66 (3H, s), 1.30 (9H, s), 1.18 (3H, d).
82%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 452-tert-Butoxycarbonylamino-propionic acid methyl ester Boc-D-Ala-OH (4.0 g, 21 mmol) and potassium carbonate (11.7 g, 84.6 mmol) was dissolved in dimethylformamide (90 mL) and iodomethane (1.6 mL, 25 mmol) was added to the reaction mixture. The reaction was allowed to stir at room temperature. overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with portions of water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound as a colorless oil (3.53 g, 82%).1H NMR (300 MHz, CDCl3): delta (ppm) 5.14 (broad s, 1 h), 4.33 (broad s, 1H), 3.51 (s, 3H), 1.49 (s, 9H).

References: [1]Patent: WO2016/8946,2016,A1 .Location in patent: Page/Page column 72-73.
[2]Patent: US2007/259860,2007,A1 .Location in patent: Page/Page column 34.
[3]Journal of Organic Chemistry,1987,vol. 52,p. 1252 - 1255.
[4]Angewandte Chemie - International Edition,2012,vol. 51,p. 5239 - 5243.

3
[ 4530-20-5 ]
[ 6404-26-8 ]
[ 3744-87-4 ]
[ 55297-72-8 ]
Boc-Ala-OH [ No CAS ]
[ 76491-51-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 1424 - 1446.

4
[ 4530-20-5 ]
[ 6404-26-8 ]
[ 3744-87-4 ]
[ 55297-72-8 ]
Boc-Ala-OH [ No CAS ]
[ 76491-50-4 ]

References: [1]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 1424 - 1446.

5
[ 186581-53-3 ]
[ 3744-87-4 ]
[ 91103-47-8 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 9691 - 9693.

6
[ 3744-87-4 ]
[ 1479-58-9 ]
(R)-{1-[4-bromo-2-(2-fluoro-benzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
[ 2387-23-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 8.5h;	{1-[4-Bromo-2-(2-fluorobenzoyl)-phenylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 136; To a stirred solution of (2-amino-5-bromophenyl)-(2'-fluoro-phenyl)-methanone 115 (60 g, 204 mmol) and the N-Boc-D-alanine 129 (38.59 g, 204 mmol) in CH2Cl2 (500 mL) was added dicyclohexylcarbodiimide (DCC) (42.09 g, 204 mmol) in CH2Cl2 (200 mL) dropwise, over a 30 min period at 0° C. The reaction mixture was allowed to stir an additional 8 h at rt. The dicyclohexyl urea which formed was filtered off and the filtrate concentrated under reduced pressure. The crude solid product 136 was purified by recrystallization from hexane and EtoAc to afford 136 (73 g, 77percent). mp 158-159° C.; IR (KBr, cm-1) 3332, 2931, 255, 1694, 1643, 1613, 1582, 1537, 1450; 1H NMR (CDCl3) delta 11.68 (s, 1H), 8.71 (d, J=9.0 Hz, 1H), 7.69 (dd, J=9.0, 2.3 Hz, 1H), 7.55-7.62 (m, 2H), 7.46 (td, J=7.6, 1.4 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (t, J=9.1 Hz, 1H), 5.13 (b, 1H), 4.37 (b, 1H), 1.51 (d, J=7.2 Hz, 3H), 1.45 (S, 9H). MS (EI) m/e (relative intensity) 467 (M++2, 14), 466 (M++1, 44), 465 (M+, 14), 464 (42), 329 (15), 321 (60), 295 (100), 224 (26); [alpha]26D=59.6 (c 0.51, EtOAc).

References: [1]Patent: US2006/3995,2006,A1 .Location in patent: Page/Page column 65-66.

7
[ 3744-87-4 ]
[ 17664-93-6 ]
[ 1207335-46-3 ]

References: [1]Helvetica Chimica Acta,2009,vol. 92,p. 2698 - 2721.

8
[ 3744-87-4 ]
[ 74-88-4 ]
[ 13734-31-1 ]

References: [1]British Journal of Pharmacology,2016,p. 2657 - 2668.
[2]Helvetica Chimica Acta,2012,vol. 95,p. 973 - 982.

9
Fmoc-D-allo-MeIle-OH [ No CAS ]
[ 3744-87-4 ]
[ 35661-60-0 ]
[ 109425-51-6 ]
[ 104091-08-9 ]
C₅₄H₇₃N₇O₁₀ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7739 - 7741.

10
[ 3744-87-4 ]
[ 13130-79-5 ]
[ 1452573-04-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl acetamide; at 20℃; for 72h;	HATU (7.5 g, 19.7 mmol) is added to a mixture of l-bromoisoquinolin-3-amine (2.0 g, 9.0 mmol), 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (1.7 g, 9.0 mmol) and DIPEA (3.4 ml, 200 mmol) in DMA (10 ml). After stirring for 3 days at RT the mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 3.3 g (94%). HPLC-MS: M-H=392/394; tR=1.97 min (*Method_l).
94%	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 N,N-dimethyl acetamide; at 20℃; for 72h;	B4a) tert-butyl-N-[1-[(1-bromoisoquinolin-3-yl)amino]-1-oxopropan-2-yl]carbamate HATU (7.5 g, 19.7 mmol) is added to a mixture of <strong>[13130-79-5]1-bromoisoquinolin-3-amine</strong> (2.0 g, 9.0 mmol), 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (1.7 g, 9.0 mmol) and DIPEA (3.4 ml, 200 mmol) in DMA (10 ml). After stirring for 3 days at RT the mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 3.3 g (94%). HPLC-MS: M-H=392/394; tR=1.97 min (*Method-1).

References: [1]Patent: WO2013/127729,2013,A1 .Location in patent: Page/Page column 50; 51.
[2]Patent: US2013/225567,2013,A1 .Location in patent: Paragraph 0253; 0254.

11
[ 3744-87-4 ]
[ 18107-18-1 ]
[ 91103-47-8 ]

References: [1]MedChemComm,2015,vol. 6,p. 300 - 305.

12
[ 3744-87-4 ]
[ 97682-44-5 ]
camptothecin [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2690 - 2693.

13
[ 13734-41-3 ]
[ 13139-15-6 ]
[ 15761-38-3 ]
[ 3744-87-4 ]
[ 15260-10-3 ]
[ 13836-37-8 ]
C₁₀₆H₁₅₇ClN₁₉O₂₃PolS [ No CAS ]
[ 73821-95-1 ]
[ 18942-49-9 ]
[ 73821-97-3 ]
[ 6404-28-0 ]
[ 108-24-7 ]
[ 55260-24-7 ]
Boc-C^αMeLeu-OH [ No CAS ]
[ 25024-53-7 ]
cyclo(30−33)[D-Phe¹², Nle^21,38,D-Ala^27,40,Glu³⁰,Lys³³]-acetyl-{human/rat corticotropin releasing factor}(9−41) [ No CAS ]