[ CAS No. 200124-22-7 ] {[proInfo.proName]}

Name: 200124-22-7|(S)-2-((tert-Butoxycarbonyl)amino)-5-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)guanidino)pentanoic acid|97%
Brand: Ambeed
SKU: A182338
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2D 3D

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Quality Control of [ 200124-22-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 200124-22-7 ]

SDS Specification

Alternatived Products of [ 200124-22-7 ]

Product Details of [ 200124-22-7 ]

CAS No. :	200124-22-7	MDL No. :	MFCD00236821
Formula :	C₂₄H₃₈N₄O₇S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CVFXPOKENLGCID-KRWDZBQOSA-N
M.W :	526.65	Pubchem ID :	11341472
Synonyms :		Chemical Name :	(S)-2-((tert-Butoxycarbonyl)amino)-5-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)guanidino)pentanoic acid

Safety of [ 200124-22-7 ]

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 [ 200124-22-7 ]

* 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 [ 200124-22-7 ]
Downstream synthetic route of [ 200124-22-7 ]

[ 200124-22-7 ] Synthesis Path-Upstream 1~1

1
[ 24424-99-5 ]
[ 200115-86-2 ]
[ 200124-22-7 ]

Reference： [1] Patent: WO2013/70688, 2013, A1, . Location in patent: Page/Page column 13; 80; 81

[ 200124-22-7 ] Synthesis Path-Downstream 1~62

1
[ 1126-09-6 ]
[ 200124-22-7 ]
[ 1221593-74-3 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 9 Synthesis of 1-[boc-Arg(Pbf)]-piperidine-4-carboxylic acid ethyl ester (I) To a solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (3.4 g, 6.36 mmol) and HATU (2.9 g, 7.63 mmol) in DMF (15 mL) was added DIEA (7.4 mL, 42.4 mmol) and the reaction mixture was stirred for 10 min at room temperature. A solution of ethyl isonipecotate (1.0 g, 6.36 mmol) in DMF (6 mL) was added to the reaction mixture dropwise. The reaction mixture was stirred at room temperature for 1 h, then diluted with ethyl acetate (150 mL) and poured into water (500 mL). The product was extracted with ethyl acetate (2*100 mL). Organic layer was washed with aqueous 0.1 N HCl (200 mL), 2% aqueous sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL). The organic layer was dried over sodium sulfate, filtered, and then evaporated in vacuo. The resultant oily product was dried in vacuo overnight to give compound I (3.7 g, 5.57 mmol) as a viscous solid. LC-MS [M+H] 666.5 (C32H51N5O8 S+H, calc: 666.7).

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 99-100

2
[ 120-43-4 ]
[ 200124-22-7 ]
[ 1221593-71-0 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 6: Synthesis of 4-[(S)-5-({Amino-[(E)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentanoyl]-piperazine-1-carboxylic acid ethyl ester (F); To a solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (13.3 g, 25.3 mmol) in DMF (10 mL) was added DIEA (22.0 mL, 126.5 mmol) at room temperature and stirred for 15 min. The reaction mixture was then cooled to 5 C. and HATU (11.5 g, 30.3 mmol) was added in portions and stirred for 30 min, followed by the dropwise addition of ethyl-1-piperazine carboxylate (4.0 g, 25.3 mmol) in DMF (30 mL). After 40 min, the reaction mixture was diluted with EtOAc (400 mL) and poured in to H2O (1 L). Extracted with EtOAc (2×400 mL) and washed with H2O (800 mL), 2% H2SO4 (500 mL), H2O (2×800 mL) and brine (800 mL). Organic layer was separated, dried over MgSO4 and solvent removed in vacuo. The resultant oily residue was dried in vacuo to afford compound F (16.4 g, 24.5 mmol) as foamy solid. LC-MS [M+H] 667.2 (C31H50N6O8S+H, calc: 667.8). Compound F was used without further purification.
16.4 g		To a solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (13.3 g, 25.3 mmol) in DMF (10 mL) was added DIEA (22.0 mL, 126.5 mmol) at room temperature and stirred for 15 min. The reaction mixture was then cooled to ~5 C and HATU (11.5 g, 30.3 mmol) was added in portions and stirred for 30 min, followed by the dropwise addition of ethyl-1-piperazine carboxylate (4.0 g, 25.3 mmol) in DMF (30 mL). After 40 min, the reaction mixture was diluted with EtOAc (400 mL) and poured into H2O (1 L). Extracted with EtOAc (2 x 400 mL) and washed with H2O (800 mL), 2% H2SO4 (500 mL), H2O (2 x 800 mL) and brine (800 mL). Organic layer was separated, dried over MgSO4 and solvent was removed in vacuo. The resultant oily residue was dried in vacuo to afford compound F (16.4 g, 24.5 mmol) as foamy solid. LC-MS [M+H] 667.2 (C31H50N6O8S+H, calc: 667.8). Compound F was used without further purification.

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 98
[2]Patent: JP2016/41698,2016,A .Location in patent: Paragraph 0035; 0036

3
[ 200124-22-7 ]
[ 162576-01-4 ]
[ 1048360-18-4 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 24 Synthesis of {(S)-4-({amino-[(E)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl}-amino)-1-[2-(benzyloxycarbonyl-methyl-amino)-ethyl carbamoyl]-butyl}-carbamic acid tert-butyl ester (AA) A solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (3.33 g, 6.32 mmol), HATU (2.88 g, 7.58 mmol) and DIEA (7.4 mL, 31.6 mmol) in DMF (40 mL) was maintained at room temperature for 20 min, followed by the addition of compound C hydrochloride (1.45 g, 6.95 mmol). Stirring was continued for additional 1 h. The reaction mixture was diluted with EtOAc (500 mL) and extracted with water (3*75 mL) and brine (75 mL). The organic layer was dried over MgSO4 and then evaporated to provide compound AA (4.14 g, 5.77 mmol) as yellowish amorphous solid. LC-MS [M+H] 717.6 (C35H52N6O8S+H, calc: 717.9).

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 108

4
[ 200124-22-7 ]
[ 162576-01-4 ]
[ 1048360-18-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1.33333h;Cooling with ice;	Preparation 57: Synthesis of {2-[boc-Arg(Pbf)]-aminoethyl}-methyl-carbamic acid benzyl ester (D); A solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (16.0 g, 30.4 mmol), compound C hydrochloride (8.2 g, 33.4 mmol) and DIEA (16.9 mL, 97.2 mmol) in DMF (150 mL) was cooled in an ice bath followed by the addition of a solution of HATU (13.8 g, 36.4 mmol) drop wise over 20 min. The temperature of the reaction mixture was raised to ambient temperature and stirring was continued for an additional 1 h. The reaction mixture was diluted with EtOAc (1 L) and extracted with water (3×200 mL) and brine (200 mL). The organic layer was dried over MgSO4 and evaporated to provide compound D (24.4 g, yield exceeded quantitative) as a yellowish oil. LC-MS [M+H] 717.4 (C35H52N6O8S+H, calc: 717.9). Compound D was used directly in the next reaction without purification as a dioxane solution.
24.4 g	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-formamide; at 20℃; for 1.33333h;	Boc-Arg (Pbf) -OH (16.0 g, ca. 30.4 mmol) in DMF (150 mL)Compound CA solution of hydrochloride (8.2 g, 33.4 mmol) and DIEA (16.9 mL, 97.2 mmol) was cooled in an ice bath followed by a solution of HATU (13.8 g, 36.4 mmol) dropwise In 20 minutes. The temperature of the reaction mixture was raised to ambient temperature and stirring was continued for an additional hour. The reaction mixture was diluted with EtOAc (1 L) and extracted with water (3 × 200 mL) and brine (200 mL). The organic layer was dried over MgSO 4 and evaporated to give compound D (24.4 g, yield exceeding the quantitative value) as a yellowish oil.

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 133
[2]Patent: JP2016/41698,2016,A .Location in patent: Paragraph 0364; 0367

5
[ 126955-78-0 ]
[ 200124-22-7 ]
[ 1221593-61-8 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 47: Synthesis of {2-[Boc-Arg(Pbf)]-aminoethyl}-ethyl-carbamic acid benzyl ester (AAA); To a solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (10.0 g, 18.98 mmol) and DIPEA (10.6 mL, 60.74 mmol) in DMF (100 mL) was added HATU (7.21 g, 18.98 mmol); the mixture was stirred at 5 C. for 15 min. To this reaction mixture, compound SS (5.40 g, 24.32 mmol), produced as described herein (Preparation 41) was added and stirred at ambient temperature for 2 h. Next, the reaction mixture was diluted with ethyl acetate (750 mL) and extracted with water (2×500 mL) and brine (500 mL). The organic layer was dried over anhydrous Na2SO4, filtered and then evaporated to give an oily residue, which was dried overnight in vacuo to give compound AAA (20.0 g) as an off-white solid. LC-MS [M+H] 731.9 (C36H54N6O8S+H, calc: 731.3). Purity>95% (UV/254 nm). Compound AAA was used without purification.

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 119

6
[ 1221593-60-7 ]
[ 200124-22-7 ]
[ 1221593-61-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h;	Preparation 35 Synthesis of {2-[boc-Arg(Pbf)]-aminoethyl}-ethyl-carbamic acid benzyl ester (MM) A solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (3.0 g, 5.69 mmol), compound LL (1.62 g, 6.26 mmol), DIEA (3.17 mL, 18.21 mmol) and HATU (2.59 g, 6.83 mmol) in DMF (20 mL) was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc (300 mL) and extracted with water (3*75 mL) and brine (75 mL). The organic layer was dried over MgSO4, filtered and then evaporated to provide compound MM (5.97 g, yield exceeded quantitative) as yellowish oil. LC-MS [M+H] 731.5 (C36H54N6O8S+H, calc: 731.7).

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 113

7
[ 1276121-70-0 ]
[ 200124-22-7 ]
[ 1276121-71-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 5 - 20℃; for 0.833333h;	Preparation 68 Synthesis of {2-[boc-Arg(Pbf)]-aminomethyl}-ethyl carbamic acid hydrocodone ester (F) Compound E (2.0 g, 4.0 mmol), <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (2.0 g, 3.8 mmol) and HATU (1.7 g, 4.3 mmol) were dissolved in DMF (40 mL), brought to ~5 C. and treated drop wise with DIPEA (3.2 mL, 18.1 mmol) over 10 min. The reaction mixture was stirred at ~5 C. for an additional 10 min and then warmed to ambient temperature, followed by stirring for 30 min. The reaction was then diluted with EtOAc (200 mL) and poured into water (250 mL). The layers were separated, the aqueous extracted with EtOAc (2150 mL) and the combined organic layers washed with 2% aq. H2SO4 (30 mL), water (2250 mL) and brine (250 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give compound F (3.0 g, 3.2 mmol, 83%) as a yellowish foamy solid. LC-MS [M+H] 908.7 (C46H65N7O10S+H, calc: 909.1).

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 136

8
[ 200124-22-7 ]
[ 1221593-72-1 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: JP2016/41698,2016,A

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[ 200124-22-7 ]
[ 1221593-73-2 ]

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[2]Patent: JP2016/41698,2016,A

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[ 200124-22-7 ]
[ 1276121-39-1 ]

Reference： [1]Patent: US2011/262355,2011,A1

11
[ 200124-22-7 ]
[ 959154-50-8 ]

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12
[ 200124-22-7 ]
[ 1048360-19-5 ]

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13
[ 200124-22-7 ]
[ 1276121-38-0 ]

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14
[ 200124-22-7 ]
[ 1345596-37-3 ]

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15
[ 200124-22-7 ]
[ 1221593-76-5 ]

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16
[ 200124-22-7 ]
[ 1221593-77-6 ]

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17
[ 200124-22-7 ]
[ 1276121-40-4 ]

Reference： [1]Patent: US2011/262355,2011,A1

18
[ 200124-22-7 ]
[ 1221593-53-8 ]

Reference： [1]Patent: US2011/262355,2011,A1

19
[ 200124-22-7 ]
[2-((S)-2-amino-5-guanidino-pentanoylamino)-ethyl]-methyl-carbamic acid hydromorphyl ester hydrochloride [ No CAS ]

Reference： [1]Patent: US2011/262355,2011,A1

20
[ 200124-22-7 ]
[ 1221593-62-9 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1221593-63-0 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1221593-64-1 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1221593-65-2 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1221593-39-0 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: US2011/262355,2011,A1

25
[ 200124-22-7 ]
[2-(2-acetylamino-5-guanidino-pentanoylamino)-ethyl]-ethyl-carbamic acid hydromorphone ester hydrochloride [ No CAS ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: US2011/262355,2011,A1

26
[ 200124-22-7 ]
[ 1343495-76-0 ]

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[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1343495-77-1 ]

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[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1343495-78-2 ]

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[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1343495-79-3 ]

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[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1343495-80-6 ]

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[2]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[2-(2-malonyl-5-guanidino-pentanoylamino)-ethyl]-ethyl-carbamic acid hydromorphone ester dihydrochloride [ No CAS ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: US2011/262355,2011,A1

32
[ 200124-22-7 ]
[ 1276121-52-8 ]

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[ 200124-22-7 ]
[ 1048360-17-3 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: JP2016/41698,2016,A

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[ 200124-22-7 ]
[ 1276122-67-8 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: JP2016/41698,2016,A

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[ 200124-22-7 ]
[ 1276121-61-9 ]

Reference： [1]Patent: US2011/262355,2011,A1
[2]Patent: JP2016/41698,2016,A

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[ 200124-22-7 ]
[ 1276121-63-1 ]

Reference： [1]Patent: US2011/262355,2011,A1

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[ 200124-22-7 ]
[ 1421423-97-3 ]

Reference： [1]Patent: US2011/262355,2011,A1

38
[ 200124-22-7 ]
N-{(S)-4-guanidino-1-[2-(methyl-[(5R,9R,13S,14S)-4,5a-epoxy-6,7-didehydro-14-hydroxy-3-methoxy-17-methylmorphinan-6-oxy]carbonyl-amino)-ethylcarbamoyl]-butyl}-malonamic acid hydrochloride [ No CAS ]

Reference： [1]Patent: US2011/262355,2011,A1

39
[ 200124-22-7 ]
[ 1276121-72-2 ]

Reference： [1]Patent: US2011/262355,2011,A1

40
[ 200124-22-7 ]
[ 1276121-74-4 ]

Reference： [1]Patent: US2011/262355,2011,A1

41
[ 200124-22-7 ]
N-((S)-1-{2-[(dihydrocodein-6-enyloxycarbonyl)-methylamino]-ethylcarbamoyl-4-guanidino}-butyl)-malonamic acid hydrochloride [ No CAS ]

Reference： [1]Patent: US2011/262355,2011,A1

42
[ 200124-22-7 ]
oxycodone 6-(N-methyl-N-(2-amino)ethylcarbamate) bis-trifluoroacetate [ No CAS ]
[ 1276121-51-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h;	Preparation 52 Synthesis of oxycodone 6-(N-methyl-N-(2-N'-Boc-arginyl(Pbf)amino))ethylcarbamate (P-3) Oxycodone 6-(N-methyl-N-(2-amino)ethylcarbamate-2TFA (7.3 g, 11.4 mmol), (E-9) prepared as described in the Example herein, was dissolved in dimethylformamide (DMF) (60 mL). <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (6.0 g, 11.4 mmol), HATU (4.75 g, 12.5 mmol) and diisopropylethylamine (DIPEA) (6.0 mL, 34.4 mmol) were added in this order. The reaction was stirred at room temperature for 2 h. The mixture was then concentrated in vacuo and the residue was partitioned between EtOAc/water (100 mL/60 mL). The organic layer was washed with water (60 mL), brine (50 mL), dried over Na2SO4 and concentrated to afford crude P-3 (11.0 g).

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 130-131

43
[ 200124-22-7 ]
C₂HF₃O₂*C₂₉H₄₁N₃O₇ [ No CAS ]
[ 1276121-81-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 5 - 20℃; for 2h;	Preparation 76: Synthesis of Intermediate (G); Compound F (1.8 g, 2.6 mmol) was dissolved in DMF (20 mL) with stirring. <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (1.4 g, 2.7 mmol), HATU (1.1 g, 2.9 mmol) and DIPEA (1.4 mL, 8.0 mmol) were added with stirring. The reaction was continued at ambient temperature for 2 h. The mixture was then concentrated, and the residue was partitioned between EtOAc and water (30 mL/20 mL). The organic layer was separated, washed with water (20 mL), brine (20 mL), dried over Na2SO4 and concentrated to afford crude compound G (1.5 g, 1.4 mmol, 54%). MS: (m/z) calc: 1052.3, observed (M+H+) 1053.9. Compound G was used without further purification.

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 139

44
[ 1276121-86-8 ]
[ 200124-22-7 ]
[ 1276540-77-2 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 82: ({(S)-2-[(S)-5-({Amino-[(Z)-2,2,4,6,7-pentamethyl-2,3-dihydro-benzofuran-5-sulfonylimino]-methyl}-amino)-2-tert-butoxycarbonylamino-pentanoylamino]-3-[methyl-(2-nitro-benzenesulfonyl)-amino]-propionyl}-methyl-amino)-acetic acid ethyl ester (E); To a solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (7.3 g, 13.8 mmol), DIPEA (7.7 mL, 44.2 mmol) in DMF (35 mL) was added HATU (5.8 g, 15.2 mmol) and stirred at 5 C. for 15 min. To this reaction mixture, compound D (6.3 g, 13.8 mmol) was added and stirred at ambient temperature for 1 h. DMF was then removed in vacuo to a total volume of 15 mL. The reaction mixture was diluted with EtOAc (250 mL) and poured into water (500 mL), extracted with EtOAc (2×250 mL), and washed with 2% aqueous H2SO4 (150 mL), water (150 mL) and brine (150 mL). The organic layer was dried over anhydrous Na2SO4, filtered and then evaporated to give an oily residue, which was dried overnight under high vacuum to give compound E (7.4 g, 59%) as an off-white solid. LC-MS [M+H] 911.5 (C39H58N8O13S+H, calc: 912.05). Purity >95% (UV/254 nm). Compound E was used without further purification.

Reference： [1]Patent: US2011/262355,2011,A1 .Location in patent: Page/Page column 142-143

45
N^α-Fmoc-Arg(N^g-Pbf)-OH [ No CAS ]
[ 200124-22-7 ]

Reference： [1]Patent: WO2013/70688,2013,A1

46
[ 24424-99-5 ]
[ 200115-86-2 ]
[ 200124-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In 1,4-dioxane; water; for 19h;	To the aqueous phase containing crude amine 3b was added sodium hydroxide (1 M aqueous, 6 mL, 6 mmol, 2 equiv). Di-fe /-butyl dicarbonate (864 mg, 3.97 mmol, 1.3 equiv) was dissolved in dioxane (20 mL, 0.15 M) and added. The mixture was stirred (19 h), concentrated under reduced pressure, diluted with water (30 mL) and sodium carbonate (5% aqueous, 3 mL, producing pH = 9), washed with ether (40 mL), acidified with hydrochloric acid (1 M aqueous, until pH = 1), extracted with ethyl acetate (3 x 30 mL), and dried with sodium sulfate. Volatiles were removed under reduced pressure to yield pure carbamate 3c (quantitative), a fraction of which was used directly in the next step. Product analysis is consistent with commercially available material.5 1H NMR (CDC13, 400 MHz) 6.58-6.30 (m, 3H), 5.65-5.55 (brs, 1H), 4.25 (q, J= 6.6 Hz, 1H), 3.25-3.10 (brs, 2H), 2.93 (s, 2H), 2.53 (s, 3H), 2.47 (s, 3H), 2.07 (s, 3H), 1.95- 1.55 (m, 4H), 1.44 (s, 6H), 1.41 (s, 9H).

Reference： [1]Patent: WO2013/70688,2013,A1 .Location in patent: Page/Page column 13; 80; 81

47
[ 200124-22-7 ]
[ 1351636-90-2 ]

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48
[ 200124-22-7 ]
[ 1351636-92-4 ]

Reference： [1]Patent: WO2013/70688,2013,A1

49
[ 200124-22-7 ]
[ 6638-79-5 ]
[ 873204-12-7 ]

Yield	Reaction Conditions	Operation in experiment
623 mg	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; for 18h;	Synthesis of amide 3d Into a flask were added one third of crude acid 3c (1.0 mmol, 1 equiv), N,O-dimethylhydroxylamine hydrochloride (195 mg, 2.00 mmol, 2 equiv), EDC hydrochloride (250 mg, 1.30 mmol, 1.3 equiv), HOBt hydrate (230 mg, 1.50 mmol, 1.5 equiv), acetonitrile (4 mL, 0.3 M), and N-methylmorpholine (165 mu, 1.50 mmol, 1.5 equiv). The mixture was stirred (18 h), diluted with ethyl acetate (40 mL), washed with sodium chloride (50% saturated aqueous, 30 mL), a mixture (1 :1, 30 mL) of citric acid (5% aqueous) and brine, a mixture (1 :1, 30 mL) of sodium bicarbonate (saturated) and sodium carbonate 5 <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> can be purchased from Sigma-Aldrich. (10% aqueous), and again with sodium chloride (50% aqueous), and dried with sodium sulfate. Volatiles were removed under reduced pressure to yield nearly pure amide 3d (530 mg, 0.93 mmol, 93% yield from carbamate 3a). Alternately, amide 3d can be prepared by first performing the amide coupling and then exchanging the amine protecting group. The crude material obtained from 1.5 mmol of starting carbamate 3a was purified by column chromatography (50 mL silica gel, 3:1 EtOAc/DCM) to yield amide 3d (623 mg, 1.09 mmol, 73% yield). ]H NMR signals were assigned by 'Eta- Eta COSY. 1H NMR (CDC13, 500 MHz) £6.40-2.22 (brs, 1H, guanidineNH), 6.18-6.06 (brs, 2H, guanidine-NH2), 5.47 (d, J= 8.3 Hz, 1H, Boc-NH), 4.68-4.58 (m, 1H, Arg-a), 3.72 (s, 3H, OMe), 3.40-3.30 (m, 1H, Arg-delta), 3.21-3.10 (m, 1H, Arg-delta), 3.18 (s, 3H, NMe), 2.94 (s, 2H, Pbf), 2.57 (s, 3H, Pbf), 2.51 (s, 3H, Pbf), 2.08 (s, 3H, Pbf), 1.75-1.52 (m, 4H, Arg-beta, Arg-gamma), 1.45 (s, 6H, Pbf), 1.41 (s, 9H, Boc); I3C NMR (CDC13, 125 MHz) £ 172.58, 158.56, 156.15, 138.27, 133.05, 132.20, 124.45, 1 17.33, 86.24, 80.01, 61.56, 49.67, 43.19, 40.78, 32.03, 30.71, 28.70, 28.53, 29.29, 28.12, 24.89, 19.19, 17.82, 12.39; IR (film, cm"') 3338, 2978, 2929, 1712, 1650, 1621, 1548, 1168, 1107; HRMS calculated for [C26H42N507SH]+, requires mlz = 570.2956, found mlz = 570.2957 (ESI); TLC (2:1) EtOAc/DCM, permanganate, R = 0.28.

Reference： [1]Patent: WO2013/70688,2013,A1 .Location in patent: Page/Page column 13; 81; 82

50
[ 200124-22-7 ]
[ 1603836-24-3 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 1836 - 1840

51
[ 200124-22-7 ]
[ 1603836-25-4 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 1836 - 1840

52
[ 6066-82-6 ]
[ 200124-22-7 ]
[ 552301-29-8 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 1836 - 1840

53
[ 200124-22-7 ]
[ 1603836-41-4 ]
[ 1603836-24-3 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 1836 - 1840

54
[ 200124-22-7 ]
1-[Arg(Pbf)]-piperidine-4-carboxylic acid ethyl ester HCl salt [ No CAS ]

Reference： [1]Patent: JP2016/41698,2016,A

55
[ 200124-22-7 ]
[ 1221593-76-5 ]

Reference： [1]Patent: JP2016/41698,2016,A

56
[ 200124-22-7 ]
[ 1221593-77-6 ]

Reference： [1]Patent: JP2016/41698,2016,A

57
[ 200124-22-7 ]
(S)-ethyl 1-(5-guanidino-2-(2,4,6-triisopropylphenylsulfonamido)pentanoyl)piperidine-4-carboxylate hydrochloride [ No CAS ]

Reference： [1]Patent: JP2016/41698,2016,A

58
[ 200124-22-7 ]
N-{(S)-4-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonylguanidino)-1-[2-(methyl-[(5R,9R,13S,14S)-4,5a-epoxy-6,7-didehydro-14-hydroxy-3-methoxy-17-methylmorphinan-6-oxy]carbonylamino)ethylcarbamoyl]butyl}malonamic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: JP2016/41698,2016,A

59
[ 200124-22-7 ]
N-{(S)-4-guanidino-1-[2-(methyl-[(5R,9R,13S,14S)-4,5a-6,7-didehydro-14-hydroxy-3-methoxy-17-methylmorphinan-6-oxy]carbonylamino)ethylcarbamoyl]butyl} malonamic acid hydrochloride [ No CAS ]

Reference： [1]Patent: JP2016/41698,2016,A

60
[ 200124-22-7 ]
C₃₁H₄₃N₇O₉*(x)ClH [ No CAS ]

Reference： [1]Patent: JP2016/41698,2016,A

61
[ 1126-09-6 ]
[ 200124-22-7 ]
[ 1221593-74-3 ]

Yield	Reaction Conditions	Operation in experiment
3.7 g		To a solution of <strong>[200124-22-7]Boc-Arg(Pbf)-OH</strong> (3.4 g, 6.36 mmol) and HATU (2.9 g, 7.63 mmol) in DMF (15 mL) was added DIEA (7.4 mL, 42.4 mmol) and the reaction mixture was stirred for 10 min at room temperature. A solution of ethyl isonipecotate (1.0 g, 6.36 mmol) in DMF (6 mL) was added to the reaction mixture dropwise. The reaction mixture was stirred at room temperature for 1 h, then diluted with EtOAc (150 mL) and poured into water (500 mL). The product was extracted with EtOAc (2 x 100 mL). The organic layer was washed with aqueous 0.1 N HCl (200 mL), 2% aqueous sodium bicarbonate (200 mL), water (200mL) and brine (200 mL). The organic layer was then dried over sodium sulfate, filtered, and then evaporated in vacuo. The resultant oily product was dried in vacuo overnight to give compound I (3.7 g, 5.57 mmol) as a viscous solid. LC-MS [M+H] 666.5 (C32H51N5O8 S+H, calc: 666.7). Compound I was used without further purification.

Reference： [1]Patent: JP2016/41698,2016,A .Location in patent: Paragraph 0340

62
[ 200124-22-7 ]
(S)-ethyl 4-(5-guanidino-2-(2,4,6-triisopropylphenylsulfonamido)pentanoyl)piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: JP2016/41698,2016,A

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[ 200124-22-7 ]

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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H226	Flammable liquid and vapour
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 200124-22-7 ] {[proInfo.proName]}

Quality Control of [ 200124-22-7 ]

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Product Details of [ 200124-22-7 ]

Safety of [ 200124-22-7 ]

Application In Synthesis of [ 200124-22-7 ]

[ 200124-22-7 ] Synthesis Path-Upstream 1~1

[ 200124-22-7 ] Synthesis Path-Downstream 1~62

Related Functional Groups of [ 200124-22-7 ]

Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

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Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 200124-22-7 ]