Potassium Hydroxide → HCID 19968211, compound

HRID 975944Notes

Reaction equation

HRID 975944 reaction equation
[C:1]([O:5][C:6]([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:38])[CH2:20][NH:21][C:22](=[O:37])[NH:23][CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:25][C:26]([O:28]CC)=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>CO.O>[C:1]([O:5][C:6]([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:38])[CH2:20][NH:21][C:22](=[O:37])[NH:23][CH:24]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:25][C:26]([OH:28])=[O:27])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86750516HCID 86750516, compound

Product 1

HCID 19968211HCID 19968211, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

By proceeding in a fashion similar to that described in Example 9, but starting from 3.9 g of ethyl (2RS,5SR)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}-3-phenylpropionate in solution in 60 cm3 of methanol and 0.45 g of potassium hydroxide dissolved in 20 cm3 of water and after treatment, 2.1 g of (2RS,5SR)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2oxoethyl]ureido}-3-phenylpropionic acid are obtained [proton NMR (250 MHz, DMSO D6, δ in ppm), 2 rotamers at room temperature, peak coalescence at 120° C.; 15. (bs, 9H, (CH3)3); 2.5 (t, 2H, CH2); 2.8 (t, 2H, CH2); 6.8 to 7.60 (m, 9H, aromatic). Infrared spectrum (KBr), characteristic bands in cm-1 : 3380, 3700 to 2250 with a maximum at 2625, 3160, 3060, 3030, 2980, 2930, 2880, 1735, 1635, 1610, 1595, 1560, 1495, 1450, 1440, 1395, 1370, 1310, 1225, 1155, 905, 890, 865, 840, 790, 760, 705].

Sources & evidence

ORD record
ord-6a681ab1231a48f2a6622e4098a356c7
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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