Phenyl isocyanate → 2-{(1r,3s)-3-[2-(1-[3-Phenylpropyl]-3-phenylureido)ethoxy]cyclohexyl-oxymethyl}-6-methylbenzoic acid

HRID 1353168Notes

Reaction equation

HRID 1353168 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][O:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([O:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:14]2)[C:3]=1[C:4]([OH:6])=[O:5].[C:32]1([N:38]=[C:39]=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O>[C:26]1([CH2:25][CH2:24][CH2:23][N:22]([CH2:21][CH2:20][O:19][C@H:15]2[CH2:16][CH2:17][CH2:18][C@@H:13]([O:12][CH2:11][C:7]3[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[C:3]=3[C:4]([OH:6])=[O:5])[CH2:14]2)[C:39]([NH:38][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:40])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 588645902-methyl-6-{(1R,3S)-3-[2-(3-phenylpropylamino)ethoxy]cyclohexyloxymethyl}benzoic acid

Product 1

HCID 100531302-{(1r,3s)-3-[2-(1-[3-Phenylpropyl]-3-phenylureido)ethoxy]cyclohexyl-oxymethyl}-6-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

160 mg of 2-methyl-6-{(1R,3S)-3-[2-(3-phenylpropylamino)ethoxy]cyclohexyloxymethyl}benzoic acid are dissolved in 2 ml of dimethylformamide, and 0.1 ml of phenyl isocyanate is added. After 30 minutes, the reaction mixture is purified by RP-HPLC. This gives 54 mg of 2-{(1R,3S)-3-[2-(1-[3-phenylpropyl]-3-phenylureido)ethoxy]cyclohexyloxymethyl}-6-methylbenzoic acid as a white lyophilizate. C33H40N2O5 (544.70), MS(ESI): 545 (M+H+).

Workup

  1. customthe reaction mixture is purified by RP-HPLC

Sources & evidence

ORD record
ord-81aded93eafb4e5da99836a983abf4fb
Source dataset
uspto-grants-2007_05
Patent number
US07220876B2

Reaction notes

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