Lithium Hydroxide → (2S)-{2-[3-(4-tert-Butyl-phenoxy)-benzylamino]-5-chloro-benzoylamino}-3-(4'-cyclohexyl-biphenyl-4-yl)-propionic Acid

HRID 1245110Notes

Reaction equation

HRID 1245110 reaction equation
C[O:2][C:3](=[O:53])[C@@H:4]([NH:24][C:25](=[O:52])[C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([O:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:44][CH:43]=2)[CH:36]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[Li+].[OH-].C1COCC1>CO>[C:48]([C:45]1[CH:44]=[CH:43][C:42]([O:41][C:37]2[CH:36]=[C:35]([CH:40]=[CH:39][CH:38]=2)[CH2:34][NH:33][C:27]2[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:26]=2[C:25]([NH:24][C@@H:4]([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[CH:14][CH:13]=3)=[CH:8][CH:7]=2)[C:3]([OH:53])=[O:2])=[O:52])=[CH:47][CH:46]=1)([CH3:51])([CH3:49])[CH3:50]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69610081HCID 69610081, compound

Product 1

HCID 58717821(2S)-{2-[3-(4-tert-Butyl-phenoxy)-benzylamino]-5-chloro-benzoylamino}-3-(4'-cyclohexyl-biphenyl-4-yl)-propionic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared following General Procedure C using (S)-2-{2-[3-(4-tert-Butyl-phenoxy)-benzylamino]-5-chloro-benzoylamino}-3-(4′-cyclohexyl-biphenyl-4-yl)-propionic acid methyl ester (135 mg, 0.19 mmol), LiOH(aq) (2.0 N, 0.22 mL, 0.44 mmol), THF (4 mL) and MeOH (1 mL). The mixture was stirred at 0° C. for 12 h. The product was obtained as off-white solid (115 mg, 0.16 mmol, 84% yield).

Sources & evidence

ORD record
ord-51bcbf8962404743aa13e0e242a469e1
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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