Lithium Hydroxide → (1R,2S)-1-[[(1R,2R,4S)-2-[[(1S)-1-(cyclopentylcarbamoyl)-2,2-dimethyl-propyl]carbamoyl]-4-[(7-methoxy-2-phenyl-4-quinolyl)oxy]cyclopentanecarbonyl]amino]-2-vinyl-cyclopropanecarboxylic acid

HRID 2242437Notes

Reaction equation

HRID 2242437 reaction equation
C([O:3][C:4]([C@@:6]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][C@H:15]2[C:38](=[O:53])[NH:39][C@H:40]([C:45](=[O:52])[NH:46][CH:47]2[CH2:51][CH2:50][CH2:49][CH2:48]2)[C:41]([CH3:44])([CH3:43])[CH3:42])=[O:13])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])C.[Li+].[OH-]>O1CCOCC1.O>[CH:47]1([NH:46][C:45]([C@@H:40]([NH:39][C:38]([C@@H:15]2[CH2:16][C@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:18][C@H:14]2[C:12]([NH:11][C@:6]2([C:4]([OH:5])=[O:3])[CH2:8][C@H:7]2[CH:9]=[CH2:10])=[O:13])=[O:53])[C:41]([CH3:44])([CH3:42])[CH3:43])=[O:52])[CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 11422715(1R,2S)-1-{[(1R,2R,4S)-2-((S)-1-Cyclopentylcarbamoyl-2,2-dimethyl-propylcarbamoyl)-4-(7-methoxy-2-phenyl-quinolin-4-yloxy)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 11456741(1R,2S)-1-[[(1R,2R,4S)-2-[[(1S)-1-(cyclopentylcarbamoyl)-2,2-dimethyl-propyl]carbamoyl]-4-[(7-methoxy-2-phenyl-4-quinolyl)oxy]cyclopentanecarbonyl]amino]-2-vinyl-cyclopropanecarboxylic acidYield 60.4%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of 52 (14 mg, 0.019 mmol) in dioxane/H2O 1:1: (4 mL) was added 1 M LiOH (115 μL, 0.115 mmol). The solution was stirred for 24 h at room temperature. Thereafter an additional portion of LiOH (75 μL, 0.075 mmol) was added and the solution was stirred for another 24 h. After acidification to approximately pH 3 with 1 M HCl and co-evaporation with toluene the residue was purified by HPLC (MeOH/H2O 70:30 with 0.2% TFA) yielding 53 (8 mg, 60%) as a colorless solid.

Workup

  1. stirringthe solution was stirred for another 24 h
  2. customAfter acidification to approximately pH 3 with 1 M HCl and co-evaporation with toluene the residue was purified by HPLC (MeOH/H2O 70:30 with 0.2% TFA)

Sources & evidence

ORD record
ord-bc6534e4f5624dcdb44c7a3365dc519d
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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