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 10200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 10200
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]

Komponenten

6

Edukt 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

Produkt 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 esterAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-68ea8460471f4e48b86f2746409f0c7b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094778B2

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