(S)-3-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic Acid Ethyl Ester → (3S)-[[(2S,3S)-2-Acetylthio-3,4-dimethyl-1-oxopentyl]amino]-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

HRID 1489564Notes

Reaction equation

HRID 1489564 reaction equation
[NH2:1][C@H: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]([CH3:32])[CH:29]([CH3:31])[CH3:30])[C:25](O)=[O:26])(=[O:22])[CH3:21]>>[C:20]([S:23][C@@H:24]([C@@H:28]([CH3:32])[CH:29]([CH3:31])[CH3:30])[C:25]([NH:1][C@H: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 13243526(S)-3-Amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic Acid Ethyl EsterHCID 57230862(2S,3S)-2-acetylthio-3,4-dimethylpentanoic acid

Product 1

HCID 86751422(3S)-[[(2S,3S)-2-Acetylthio-3,4-dimethyl-1-oxopentyl]amino]-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-oneYield 49%

Procedure

0.500 g (1.91 mmol) of (3S)-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one and 0.430 g (2.1 mmol) of (2S,3S)-2-acetylthio-3,4-dimethylpentanoic acid were treated by the same method as that of Example 101(h). Thus, 0.420 g of the title compound was obtained.

Sources & evidence

ORD record
ord-8930e97b365648fc87b074d0e58b73bc
Source dataset
uspto-grants-1997_10
Patent number
US05679671

Reaction notes

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