Hydrochloric Acid → HCID 20699034, compound

HRID 383118Notes

Reaction equation

HRID 383118 reaction equation
C[O:2][C:3](=[O:24])[C@@H:4]1[CH2:8][CH: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].[Li+].[OH-].Cl>CO>[C:17]([N:5]1[CH2:6][CH:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:8][C@H:4]1[C:3]([OH:24])=[O:2])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 20699035HCID 20699035, compound

Product 1

HCID 20699034HCID 20699034, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.3 g (3.6 mmol) of N-Boc-4-(t-butyldimethylsilyloxy)proline methyl ester, prepared as described by Rosen et al., J. Med. Chem. 1988, 31, 1598, in 10 ml of methanol was added 5 ml (5 mmol) of 1 N LiOH in an ice bath. The reaction mixture was stirred for 30 min. The reaction mixture was adjusted to pH 2-3 with 1 N HCl at the same temperature and the solvent was evaporated. The resulting residue was partitioned between dichloromethane and water, and extracted 3 times with dichloromethane. The combined organic solution was washed with 1 N HCl and water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 1.05 g (96%) of N-Boc-4-(t-butyldimethylsilyl-oxy)proline as a foamy solid which was used without further purification.

Workup

  1. customthe solvent was evaporated
  2. customThe resulting residue was partitioned between dichloromethane and water
  3. extractionextracted 3 times with dichloromethane
  4. washThe combined organic solution was washed with 1 N HCl and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4461ee6adbc49fea0a98a863cad78ed
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

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