Ethyl alpha-oxobenzenebutanoate → (+/-)-Dihydro-3-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-4-oxo-1,5-benzothiazepine-5(2H)acetic acid, ethyl ester

HRID 986213Notes

Reaction equation

HRID 986213 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[S:4][CH2:3]1.[CH2:20]([O:22][C:23](=[O:34])[C:24](=O)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:21].C([BH3-])#N.[Na+]>>[CH2:20]([O:22][C:23]([CH:24]([NH:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]2[CH2:16][CH:17]=[CH:18][CH:19]=[C:5]2[S:4][CH2:3]1)[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:34])[CH3:21]

Participants

4

Reactant 3

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 5003444Sodium cyanoborohydrideHCID 15591257(+/-)-3-amino-3,4-dihydro-4-oxo-1,5-benzothiazepine-5(2H)-acetic acid, ethyl ester

Product 1

HCID 86741917(+/-)-Dihydro-3-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-4-oxo-1,5-benzothiazepine-5(2H)acetic acid, ethyl ester

Procedure

(±)-3-Amino-3,4-dihydro-4-oxo-1,5-benzothiazepine-5(2H)-acetic acid, ethyl ester is reacted with ethyl-2-oxo-4-phenylbutyrate in the presence of sodium cyanoborohydride according to the procedure of Example 1(f) to yield (±)-dihydro-3-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-4-oxo-1,5-benzothiazepine-5(2H)-acetic acid, ethyl ester.

Sources & evidence

ORD record
ord-01e3a3ad61c2474ba4cf7386aa6e1ebe
Source dataset
uspto-grants-1987_12
Patent number
US04711884

Reaction notes

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