Pentanoic acid, 2-(acetylthio)-3-methyl-, (2S,3S)- → 3-[[(2S,3S)-2-Acetylthio-3methyl-1-oxopentyl]amino]-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

HRID 1489563Notes

Reaction equation

HRID 1489563 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]1=[O:19].[C:20]([S:23][C@@H:24]([C@@H:28]([CH3:31])[CH2:29][CH3:30])[C:25](O)=[O:26])(=[O:22])[CH3:21]>>[C:20]([S:23][C@@H:24]([C@@H:28]([CH3:31])[CH2:29][CH3:30])[C:25]([NH:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:3]1=[O:19])=[O:26])(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 10607714Pentanoic acid, 2-(acetylthio)-3-methyl-, (2S,3S)-HCID 132435253-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

Product 1

HCID 228783813-[[(2S,3S)-2-Acetylthio-3methyl-1-oxopentyl]amino]-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-oneYield 48.3%

Procedure

By using 0.525 g (2.00 mmol) of 3-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one and 0.418 g (2.20 mmol) of (2S,3S)-2-acetylthio-3-methylpentanoic acid obtained in the Synthesis Example C-2, the treatment of Example C-1 was repeated. Thus, 0.420 g of the title compound was obtained as a colorless amorphous product (yield 48%).

Sources & evidence

ORD record
ord-162fbcefab6b4ae7bea1dba7bf5cb3c3
Source dataset
uspto-grants-1997_10
Patent number
US05679671

Reaction notes

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