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

HRID 256036Notes

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]([CH:23]([CH3:25])[CH3:24])[N:18]([CH2:26][C:27]([OH:29])=[O:28])[C:17]1=[O:30])[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]([CH:23]([CH3:25])[CH3:24])[N:18]([CH2:26][C:27]([OH:29])=[O:28])[C:17]1=[O:30])[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 18610525alpha-{6(R)-[1(S)-Ethoxycarbonyl-3-phenylpropylamino]-3(R)-isopropyl-5-oxoperhydro-1,4-thiazepin-4-yl}acetic acid

Product 1

HCID 18610511alpha-{6(R)-[1(S)-Carboxy-3-phenylpropylamino]-3(R)-isopropyl-5-oxoperhydro-1,4-thiazepin-4-yl}acetic acidYield 75.5%

Procedure

160 mg of α-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-3(R)-isopropyl-5-oxoperhydro-1,4-thiazepin-4-yl}acetic acid (prepared as described in Example 28 above) were hydrolyzed with aqueous sodium hydroxide in the same manner as described in Example 5, giving 113 mg of the title compound as a powder.

Sources & evidence

ORD record: ord-86b4ad5d463543afa68e3403c95c5172
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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