Lithium Hydroxide → HCID 11650315, compound

HRID 1784234Notes

Reaction equation

HRID 1784234 reaction equation
C[O:2][C:3](=[O:49])[C@@H:4]([NH:26][C:27](=[O:48])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:38][CH:37]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[Li+].[OH-]>C1COCC1.CO>[C:39]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:40]=[CH:41][C:36]([CH2:35][O:34][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[C:27]([NH:26][C@@H:4]([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)=[CH:8][CH:7]=2)[C:3]([OH:49])=[O:2])=[O:48])=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 68859688HCID 68859688, compound

Product 1

HCID 11650315HCID 11650315, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-[2-(biphenyl-4-ylmethoxy)-benzoylamino]-3-[4-(biphenyl-4-ylmethoxy)-phenyl]-propionic acid methyl ester (50 mg, 0.077 mmol) was dissolved in 5 mL of THF-MeOH (4-1), cooled to 0° C. and 1.1 equiv of 2 N LiOH added. After 30 minutes, 3.2 additional equiv of 2N LiOH was added and the reaction stirred for 30 minutes. The reaction was worked up according to Procedure C to give 29 mg of the title compound.

Sources & evidence

ORD record
ord-d365ed09cedf475a99efb78cc739170f
Source dataset
uspto-grants-2009_03
Patent number
US07501538B2

Reaction notes

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