Lithium hydroxide, monohydrate → HCID 57988322, compound

HRID 1666530Notes

Reaction equation

HRID 1666530 reaction equation
[C:1]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([S:34][CH2:35][CH2:36][CH2:37][CH3:38])[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:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:2]=[CH:3][C:4]([C@@:7]2([S:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:11][N:10]([C:12](=[O:29])[C@@H:13]([NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[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 57988336HCID 57988336, compound

Product 1

HCID 57988322HCID 57988322, compoundYield 88%

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-(butylthio)pyrrolidine-2-carboxylate (135 mg, 0.217 mmol) in THF (1.5 mL) and methanol (1.500 mL) was added pre-made solution of lithium hydroxide monohydrate (18.19 mg, 0.433 mmol) in water (1.5 mL). The resulting cloudy solution was stirred at room for 3 hours. Quenched with 5% citric acid, extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated to afford the desired product (2S,4R)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-(butylthio)pyrrolidine-2-carboxylic acid (129 mg, 0.191 mmol, 88% yield) as a white foam. LC-MS (retention time: 3.67 min, method C), MS m/z 609 (M+H).

Workup

  1. customQuenched with 5% citric acid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-403590806e594d56b5f9140675d08e51
Source dataset
uspto-grants-2011_10
Patent number
US08044023B2

Reaction notes

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