Lithium hydroxide, monohydrate → HCID 59386551, compound

HRID 2358359Notes

Reaction equation

HRID 2358359 reaction equation
[C:1]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([O:34][CH3:35])[CH2:11][N:10]([C:12](=[O:29])[C@@H:13]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])[C@H:9]([C:30]([O:32]C)=[O:31])[CH2:8]2)=[CH:3][CH:2]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[C:1]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:2]=[CH:3][C:4]([C@@:7]2([O:34][CH3:35])[CH2:11][N:10]([C:12](=[O:29])[C@@H:13]([NH:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])[C@H:9]([C:30]([OH:32])=[O:31])[CH2:8]2)=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59386564HCID 59386564, compound

Product 1

HCID 59386551HCID 59386551, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-methyl 4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-methoxypyrrolidine-2-carboxylate (166 mg, 0.294 mmol) in THF (2 mL) and MeOH (2 mL) was added a pre-made solution of lithium hydroxide monohydrate (37 mg, 0.882 mmol) in water (2 mL). This cloudy solution was stirred at rt for 18 h, and then concentrated in vacuo. The residue was dissolved in water and acidified with 1N HCl to pH 2. This aqueous solution was extracted with EtOAc. The organic phase was washed with 5% citric acid and brine, dried over MgSO4, filtered, and concentrated in vacuo to give 148 mg (91%) of (2S,4R)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-methoxypyrrolidine-2-carboxylic acid as a white solid. No further purification was undertaken.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water
  3. extractionThis aqueous solution was extracted with EtOAc
  4. washThe organic phase was washed with 5% citric acid and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4cc471e61140464389e12805ce47db4a
Source dataset
uspto-grants-2010_07
Patent number
US07763584B2

Reaction notes

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