Sodium Hydroxide → alpha-{6(R)-[1(S)-Carboxy-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetic acid

HRID 256025Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 13877956alpha-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl)acetic acid

Product 1

HCID 13877958alpha-{6(R)-[1(S)-Carboxy-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetic acidYield 76.7%

Procedure

90 mg of α-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-3(S)-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetic acid (prepared as described in Example 17 above) were hydrolyzed with aqueous sodium hydroxide in the manner described in Example 5, to give 65 mg of the title compound as a powder.

Sources & evidence

ORD record: ord-1016936beed34ca68b334382fd938268
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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