HCID 86750540, compound → HCID 19968026, compound

HRID 975983Notes

Reaction equation

HRID 975983 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]1[C:19](=[O:36])[CH2:20][NH:21][C:22](=[O:35])[NH:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=1)[C:27]([O:29]CC)=[O:28]>CO>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:9]1[C:19](=[O:36])[CH2:20][NH:21][C:22](=[O:35])[NH:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=1)[C:27]([OH:29])=[O:28]

Participants

3

Reactant 1

HCID 86750540HCID 86750540, compound

Product 1

HCID 19968026HCID 19968026, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By proceeding in a fashion similar to that described in Example 9, but starting from 0.8 g of ethyl (2RS,5SR)-3-{3-{2-[2-(2-hydroxyphenyl)-5-phenyl-1-pyrrolidinyl]-2-oxoethyl}ureido}benzoate in solution in 15 cm3 of methanol and 0.27 g of potassium hydroxide in solution in 3 cm3 of water, and after treatment and recrystallization in diisopropyl ether, 0.21 g of (2RS,5SR)-3-{3-{2-[2-(2-hydroxyphenyl)-5-phenyl-1-pyrrolidinyl]-2-oxoethyl}ureido}benzoic acid, melting at about 160° C., is obtained [proton NMR (200 MHz, DMSO D6, δ in ppm), 1.8 to 2.5 (2m, 4H, CH2 --CH2); 3.3 and 4 (ABX, 2H, CH2N); 5.2 (m, 2H, 2 CHN); 6.7 to 7.4 (m, 13H, aromatic); 6.8 (bt 9(s) 9.8(bs) 12.8(vbs) (4H exchangeable, 1 OH, 1 CO2H and 2NH)], [Infrared spectrum (KBr), characteristic bands in cm-1 3400, 3070, 2980, 1695, 1630, 1560, 1490, 1460, 760, 700, 685].

Workup

  1. custom0.27 g of potassium hydroxide in solution in 3 cm3 of water, and after treatment and recrystallization in diisopropyl ether

Sources & evidence

ORD record
ord-5a3beb094440421e9cfa361734812a8c
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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