Potassium Hydroxide → HCID 86751941, compound

HRID 725883Notes

Reaction equation

HRID 725883 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[N:12]([C:13](=[O:30])[CH2:14][NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][C:26]([O:28]C)=[O:27])[CH:20]=2)=[O:17])[C@@H:11]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:10][C@H:9]1[C:38]([O:40]C)=[O:39].[OH-].[K+]>O.CO>[C:26]([CH2:25][C:21]1[CH:20]=[C:19]([NH:18][C:16](=[O:17])[NH:15][CH2:14][C:13]([N:12]2[C@H:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C@@H:9]([C:38]([OH:40])=[O:39])[CH2:10][C@@H:11]2[C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])=[O:30])[CH:24]=[CH:23][CH:22]=1)([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86751942HCID 86751942, compound

Product 1

HCID 86751941HCID 86751941, compoundYield 64.8%

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 0.6 g of 2-tert-butyl 4-methyl (2R*,4R*,5S*)-(-)-5-(2-fluorophenyl)-1-{2-[3-(3-(methoxycarbonylmethyl)phenyl)ureido]acetyl}pyrrolidine-2,4-dicarboxylate and 0.12 g of potassium hydroxide in a mixture of 10 cm3 of distilled water and 25 cm3 of methanol. After treatment, there is obtained 0.37 g of 2-tert-butyl hydrogen (2R*,4S*,5S*)-(+)-1-{2-[3-(3-(carboxymethyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)pyrrolidine-2,4-dicarboxylate, the spectroscopic analyses of which are in accordance with those of the first product of Example 52.

Sources & evidence

ORD record
ord-1594f44b1e884fceac24ca15b72de357
Source dataset
uspto-grants-1998_01
Patent number
US05707991

Reaction notes

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