Lithium Hydroxide → 5-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acid

HRID 643834Notes

Reaction equation

HRID 643834 reaction equation
C[O:2][C:3]([C:5]1[CH:9]([C:10](=[O:24])[NH:11][C@:12]2([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][C@H:13]2[CH:15]=[CH2:16])[CH2:8][CH:7]([O:25][C:26]2[C:35]3[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=3)[N:29]=[C:28]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:27]=2)[CH:6]=1)=[O:4].[Li+].[OH-]>O1CCOCC1.O>[C:20]([O:19][C:17]([C@@:12]1([NH:11][C:10]([CH:9]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]([O:25][C:26]3[C:35]4[C:30](=[CH:31][C:32]([O:36][CH3:37])=[CH:33][CH:34]=4)[N:29]=[C:28]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:27]=3)[CH2:8]2)=[O:24])[CH2:14][C@H:13]1[CH:15]=[CH2:16])=[O:18])([CH3:21])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 592041875-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acid methyl ester

Product 1

HCID 593916145-((1R,2S)-1-tert-Butoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-3-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopent-1-enecarboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

The methyl ester 30 (35 mg, 59 mmol) was dissolved in dioxane/water (1:1, 4 mL) and LiOH (1.2 mmol) was added. The reaction was stirred over night and then co-concentrated. This gave the title compound (0.32 g, 90%) as a yellow salt.

Sources & evidence

ORD record
ord-72844b94f03d48b6ad5bac44c533e718
Source dataset
uspto-grants-2010_04
Patent number
US07700552B2

Reaction notes

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