Lithium Hydroxide → HCID 68616763, compound

HRID 1893703Notes

Reaction equation

HRID 1893703 reaction equation
[CH:1]1([O:6][C:7]([NH:9][CH:10]([C:43]([CH3:46])([CH3:45])[CH3:44])[C:11]([N:13]2[CH:17]([C:18](=[O:29])[NH:19][C:20]3([C:25]([O:27]C)=[O:26])[CH2:22][CH:21]3[CH:23]=[CH2:24])[CH2:16][CH:15]([O:30][C:31]([N:33]3[CH2:41][C:40]4[C:35](=[CH:36][CH:37]=[CH:38][C:39]=4[F:42])[CH2:34]3)=[O:32])[CH2:14]2)=[O:12])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+]>C1COCC1.CO.O>[C:25]([C:20]1([NH:19][C:18]([CH:17]2[N:13]([C:11](=[O:12])[CH:10]([NH:9][C:7]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:8])[C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:14][CH:15]([O:30][C:31]([N:33]3[CH2:41][C:40]4[C:35](=[CH:36][CH:37]=[CH:38][C:39]=4[F:42])[CH2:34]3)=[O:32])[CH2:16]2)=[O:29])[CH2:22][CH:21]1[CH:23]=[CH2:24])([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68799027HCID 68799027, compound

Product 1

HCID 68616763HCID 68616763, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

4-Fluoro-1,3-dihydro-isoindole-2-carboxylic acid 1-(2-cyclopentyloxycarbonylamino-3,3-dimethyl-butyryl)-5-(1-methoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-pyrrolidin-3-yl ester (550 mg, 0.86 mmol) was dissolved in THF:MeOH:H2O (1:1:1 8.7 mL) and treated with lithium hydroxide (180 mg, 4.28 mmol). The reaction was judged complete by complete consumption of starting material after approximately 2 h, at which time the reaction was neutralized with 1N aqueous HCl. The organic phase was extracted with EtOAc then washed with saturated aqueous NaCl, and dried over sodium sulfate. After removal of solvent, 4-fluoro-1,3-dihydro-isoindole-2-carboxylic acid 5-(1-carboxy-2-vinyl-cyclopropylcarbamoyl)-1-(2-cyclopentyloxycarbonylamino-3,3-dimethyl-butyryl)-pyrrolidin-3-yl ester was obtained (540 mg, 0.86 mmol), which was used in the next reaction without further purification.

Workup

  1. customThe reaction was judged complete by complete consumption of starting material after approximately 2 h, at which time the reaction
  2. extractionThe organic phase was extracted with EtOAc
  3. washthen washed with saturated aqueous NaCl
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of solvent

Sources & evidence

ORD record
ord-2704828a8da44c92b5f09adc0ece2f03
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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