Lithium Hydroxide → HCID 68814269, compound

HRID 732383Notes

Reaction equation

HRID 732383 reaction equation
[Li+].[OH-].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH:13]([CH2:15][C:16]([O:18]C)=[O:17])[CH2:12][C@@H:11]1[C@H:20]1[O:24][C:23]([CH3:26])([CH3:25])[N:22]([C:27](=[O:29])[CH3:28])[C@H:21]1[CH2:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:14][CH:13]([CH2:15][C:16]([OH:18])=[O:17])[CH2:12][C@@H:11]1[C@H:20]1[O:24][C:23]([CH3:26])([CH3:25])[N:22]([C:27](=[O:29])[CH3:28])[C@H:21]1[CH2:30][C:31]1[CH:32]=[C:33]([F:38])[CH:34]=[C:35]([F:37])[CH:36]=1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68815003HCID 68815003, compound

Product 1

HCID 68814269HCID 68814269, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add LiOH (0.32 mL, 3M solution in water) to a solution of (R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-methoxycarbonylmethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.1 g, 0.19 mmol) in 0.32 mL of THF and stir overnight. Remove THF under reduced pressure. Add ethyl acetate and separate the layers. Acidify the aqueous layer with citric acid pH: 3) and extract with ethyl acetate. Dry over MgSO4 and concentrate under reduced pressure to provide the title compound (0.087 g, 90%).

Workup

  1. customAdd ethyl acetate and separate the layers
  2. extractionextract with ethyl acetate
  3. dry with materialDry over MgSO4
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-9adae8f111394ea7a99840bf20c72f92
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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