Triethylamine → 4-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 433090노트

반응식

HRID 433090 반응식
Cl.[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@@H:13]([NH:15][CH2:16][CH2:17][CH3:18])[CH3:14])=[CH:8][CH:7]=1)(=[O:5])=[O:4].C(N(CC)CC)C.[C:26]([O:30][C:31]([N:33]1[CH2:39][CH2:38][C:37](=[O:40])[N:36]([CH2:41][CH2:42][CH2:43][CH:44]=O)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:26]([O:30][C:31]([N:33]1[CH2:39][CH2:38][C:37](=[O:40])[N:36]([CH2:41][CH2:42][CH2:43][CH2:44][N:15]([C@@H:13]([CH3:14])[CH2:12][C:9]2[CH:10]=[CH:11][C:6]([S:3]([CH3:2])(=[O:5])=[O:4])=[CH:7][CH:8]=2)[CH2:16][CH2:17][CH3:18])[CH2:35][CH2:34]1)=[O:32])([CH3:27])([CH3:28])[CH3:29]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 113121495-Oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl esterHCID 69223624[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-propylamine hydrochloride

생성물 1

HCID 587719034-(4-{[(S)-2-(4-methanesulfonyl-phenyl)-1-methyl-ethyl]-propyl-amino}-butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester수율 97.8%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A mixture of [(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-propylamine hydrochloride (2.05 g, 7.03 mmole), triethylamine (0.98 mL, 7 mmole), 5-oxo-4-(4-oxobutyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (2.0 g, 7.03 mmole), and sodium triacetoxyborohydride (2.23 g, 10.5 mmole) in 1,2-dichloroethane (40 mL) was stirred at room temperature for 15 hours. The mixture was concentrated, and the residue was partitioned between diethyl ether and saturated sodium carbonate. The organic phase was dried (magnesium sulfate) and concentrated to give 4-(4-{[(S)-2-(4-methane-sulfonylphenyl)-1-methylethyl]propyl-amino}butyl)-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3.6 g) as a heavy syrup. M+H=524. The hydrochloride salt was recrystallized from acetone/diethyl ether, m.p. 156-158° C.

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between diethyl ether and saturated sodium carbonate
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6aa676e3eb2b4a9cae72fb7a698a5dac
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06667301B2

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