Potassium Hydroxide → (2RS,4SR,5SR)-3-{3-[2-(2-tert-butoxycarbonyl-4-(3,3-dimethylpiperidinocarbonyl)-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid

HRID 725868Notes

Reaction equation

HRID 725868 reaction equation
[CH3:1][C:2]1([CH3:46])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([CH:10]2[CH:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]([C:21](=[O:38])[CH2:22][NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([O:35]CC)=[O:34])[CH:28]=3)=[O:25])[CH:12]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:11]2)=[O:9])[CH2:3]1.[OH-].[K+]>O.CO>[C:42]([O:41][C:39]([CH:12]1[CH2:11][CH:10]([C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C:2]([CH3:46])([CH3:1])[CH2:3]2)=[O:9])[CH:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:13]1[C:21](=[O:38])[CH2:22][NH:23][C:24](=[O:25])[NH:26][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][CH:32]=1)[C:33]([OH:35])=[O:34])=[O:40])([CH3:43])([CH3:44])[CH3:45]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86751922tert-butyl (2RS,4SR,5SR)-4-(3,3-dimethylpiperidinocarbonyl)-1-{2-[3-(3-(ethoxycarbonyl)phenyl]ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate

Product 1

HCID 19709672(2RS,4SR,5SR)-3-{3-[2-(2-tert-butoxycarbonyl-4-(3,3-dimethylpiperidinocarbonyl)-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acidYield 52.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A The reaction is carried out in a way analogous to that described in Example 3, but from 2.3 g of tert-butyl (2RS,4SR,5SR)-4-(3,3-dimethylpiperidinocarbonyl)-1-{2-[3-(3-(ethoxycarbonyl)phenyl]ureido]acetyl}-5-phenylpyrrolidine-2-carboxylate and 0.2 g of potassium hydroxide in a mixture of 20 cm3 of distilled water and 50 cm3 of methanol. After treatment, there are obtained 1.16 g of (2RS,4SR,5SR)-3-{3-[2-(2-tert-butoxycarbonyl-4-(3,3-dimethylpiperidinocarbonyl)-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid [Rf =0.2; eluent=methylene chloride/methanol (97.5/2.5)].

Sources & evidence

ORD record
ord-968a85ff76c84183b410cb20eaf422dc
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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