Lithium hydroxide, monohydrate → HCID 57998008, compound

HRID 2425787Notes

Reaction equation

HRID 2425787 reaction equation
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([C@@:7]2([S:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C@H:9]([C:22]([O:24]C)=[O:23])[CH2:8]2)=[CH:3][CH:2]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[CH2:15]([O:14][C:12]([N:10]1[CH2:11][C@@:7]([C:4]2[CH:3]=[CH:2][C:1]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[CH:6][CH:5]=2)([S:26][CH2:27][Si:28]([CH3:31])([CH3:29])[CH3:30])[CH2:8][C@H:9]1[C:22]([OH:24])=[O:23])=[O:13])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57998010HCID 57998010, compound

Product 1

HCID 57998008HCID 57998008, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-benzyl 2-methyl 4-(biphenyl-4-yl)-4-((trimethylsilyl)methylthio)pyrrolidine-1,2-dicarboxylate (472 mg, 0.884 mmol) in THF (10 mL) and MeOH (10 mL) was added premade solution of Lithium hydroxide monohydrate (74.2 mg, 1.769 mmol) in Water (10 mL). The formed white slurry was stirred at room temperature for 3 days. Quenched with 5% citric acid, extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, evaporated to afford the desired product (2S,4R)-1-(benzyloxycarbonyl)-4-(biphenyl-4-yl)-4-((trimethylsilyl)methylthio)pyrrolidine-2-carboxylic acid (460 mg, 0.797 mmol, 90% yield) as a wax. This product was used for the next reaction without further purification. LC-MS (retention time: 3.43 min, method B), MS m/z 520 (M+H).

Workup

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

Sources & evidence

ORD record
ord-8e5f1734aef34e5085e068a61efccb39
Source dataset
uspto-grants-2011_06
Patent number
US07964560B2

Reaction notes

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