Sodium Hydroxide → HCID 10958909, compound

HRID 1078715Notes

Reaction equation

HRID 1078715 reaction equation
C[O:2][C:3](=[O:24])[C@@H:4]1[CH2:8][C@@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:6][N:5]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[OH-].[Na+]>CO.O>[C:20]([O:19][C:17]([N:5]1[CH2:6][C@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:12])[CH2:8][C@H:4]1[C:3]([OH:24])=[O:2])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10618477(2S,4R)-1-tert-Butyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 10958909HCID 10958909, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(2S,4R)-N-tert-Butoxycarbonyl-4-tert-butyldimethylsiloxyproline methyl ester (5.9 g, 16.5 mmol) was dissolved in methanol (45 ml) and water (11 ml). Then, 2.5N aqueous sodium hydroxide (6.6 ml, 16.5 mmol) was added thereto. The mixture was stirred at room temperature for 6 h, and then the organic solvent was distilled off. The aqueous layer was washed with ethyl acetate, then adjusted to pH 2.5 with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and concentrated in vacuo to obtain crude (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxyproline (5.1 g). ##STR384##

Workup

  1. distillationthe organic solvent was distilled off
  2. washThe aqueous layer was washed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5869af299a0400a8cd35ae0023826db
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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