Water → HCID 86592524, compound

HRID 1374425Notes

Reaction equation

HRID 1374425 reaction equation
[CH2:1]([O:4][C:5]([N:7]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[C@H:8]([CH2:18][O:19][Si](C(C)(C)C)(C)C)[CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:6])[CH:2]=[CH2:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>CO>[CH2:1]([O:4][C:5]([N:7]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[C@H:8]([CH2:18][OH:19])[CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrate2×HCID 86592525HCID 86592525, compound

Product 1

HCID 86592524HCID 86592524, compoundYield 892.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (4S)-4-[[(allyloxy)carbonyl](2-methoxy-2-oxoethyl)amino]-5-{[tert-butyl(dimethyl)silyl]oxy}pentanoate (5.29 g, 1.2 mmol) in methanol (106 ml) was added p-toluenesulfonic acid monohydrate (0.22 g, 1.2 mmol) and the mixture was stirred for 30 minutes. To the mixture was further added p-toluenesulfonic acid monohydrate (0.22 g, 1.2 mmol) and the mixture was stirred for 1 hour. The reaction mixture was poured into water and extracted three times with ethyl acetate. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified with silica gel chromatography to give tert-butyl (4S)-4-[[(allyloxy)carbonyl](2-methoxy-2-oxoethyl)amino]-5-hydroxypentanoate (3.7 g, 93%).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionextracted three times with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  5. customthe solvent was removed
  6. customThe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-59601ba22227429895f07c7a0cadd414
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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