Potassium Bromide → Potassium Hydroxide

HRID 975978Notes

Reaction equation

HRID 975978 reaction equation
[C:1]1([C@H:7]2[CH2:11][CH2:10][C@@H:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:8]2[C:18](=[O:41])[CH2:19][NH:20][C:21](=[O:40])[NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32]CC3C=CC=CC=3)=[O:31])=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K+:42].[Br-]>CO.O>[OH-:31].[K+:42].[C:12]1([C@H:9]2[CH2:10][CH2:11][C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]2[C:18](=[O:41])[CH2:19][NH:20][C:21](=[O:40])[NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([OH:32])=[O:31])=[CH:25][CH:24]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 253877Potassium BromideHCID 53964173HCID 53964173, compound

Product 2

HCID 14797Potassium HydroxideHCID 53751985HCID 53751985, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

By proceeding in a fashion similar to that described in Example 9, but starting from 4 g of benzyl cis-4-{3-[2-(2,5-diphenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylacetate in solution in 65 cm3 of methanol and 0.61 g of potassium hydroxide in solution in 12 cm3 of water, and after treatment, 1.8 g of cis-4-{3-[2-(2,5-diphenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylacetic acid, melting at 221° C., are obtained [proton NMR (200 MHz, DMSO D6, δ in ppm), 1.4 to 2.4 (m, 4H, CH2 --CH2); 3.3 (s, 2H, CH2CO2); 3.2 and 3.8 (ABX, 2H, CH2NH); 5.1 (m, 2H, 2 CHN); 6.1 (t, 1H exchangeable, NH); 6.9 (d, 2H, aromatic in para position); 7.1 to 7.4 (m, 12H, aromatic); 8.6 (s, 1H exchangeable, NH)], [infrared spectrum (KBr), characteristic bands in cm-1 3375, 3095, 3070, 3035, 2980, 2880, 1735, 1700, 1630, 1610, 1515, 1450, 1560, 805, 760, 705].

Sources & evidence

ORD record
ord-3984013ab8c2430a931d60ea92810202
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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