Potassium Bromide → Potassium Hydroxide

HRID 975982Notes

Reaction equation

HRID 975982 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:39])[CH2:19][NH:20][C:21](=[O:38])[NH:22][C:23]2[CH:28]=[CH:27][C:26]([S:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K+:40].[Br-]>CO.O>[OH-:32].[K+:40].[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:39])[CH2:19][NH:20][C:21](=[O:38])[NH:22][C:23]2[CH:24]=[CH:25][C:26]([S:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 253877Potassium BromideHCID 67713341HCID 67713341, compound

Product 2

HCID 14797Potassium HydroxideHCID 53866179HCID 53866179, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

By proceeding in a fashion similar to that described in Example 9, but starting from 1.3 g of tert-butyl cis-{4-{3-[2-(2,5-diphenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}-phenylthio}acetate in solution in 20 cm3 of methanol and 0.17 g of potassium hydroxide in solution in 4 cm3 of water, and after treatment, 0.5 g of cis-{4-{3-[2-(2,5-diphenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylthio}-acetic acid, melting at about 200° C., is obtained [proton NMR (200 MHz, DMSO D6, δ in ppm), 1.8 to 2.4 (m, 4H, CH2 --CH2); 3.35 (s, 2H, CH2S); 3.3 and 3.85 (ABX, 2H, CH2N): 5.1 (m, 2H, 2 CHN); 6.5 (t, 1H exchangeable, NH); 7.1 to 7.4 (m, 14H, aromatic); 9 (s, 1H exchangeable, NH)], [infrared spectrum (KBr), characteristic bands in cm-1 3400, 3090, 3060, 3030, 2975, 2875, 1640, 1595, 1540, 1495, 1450, 1400, 825, 760, 700].

Sources & evidence

ORD record
ord-c474c9c7f92d45dba78f1eeb30daacb2
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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