Pyridine → (2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-[(methylsulfonyl)oxy]-4-phenylbutyl acetate

HRID 651258Notes

Reaction equation

HRID 651258 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]([OH:23])[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[CH3:24][S:25](Cl)(=[O:27])=[O:26].N1C=CC=CC=1>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C@@H:6]([O:23][S:25]([CH3:24])(=[O:27])=[O:26])[C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 11056398(2S,3S)-1-Acetoxy-3-(t-butoxycarbonylamino)-2-hydroxy-4-phenylbutane

Product 1

HCID 11475108(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-[(methylsulfonyl)oxy]-4-phenylbutyl acetateYield 98.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture composed of 12.4 mmol (4.00 g) of (2S,3S)-1-acetoxy-3-(t-butoxycarbonylamino)-2-hydroxy-4-phenylbutane, 24.8 mmol (2.48 g) of methanesulfonyl chloride and 20 ml of pyridine was allowed to stand at 4° C. for 48 hours. Thereafter, 30 ml of ethyl acetate was added, the organic layer was washed with three 30-ml portions of 10% hydrochloric acid and finally with 30 ml of water. The organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. Hexane (30 ml) was added to the residue, and the mixture was allowed to stand. The resulting white solid precipitate was collected by filtration. Thus was obtained 4.90 g (98%) of the title compound.

Workup

  1. washthe organic layer was washed with three 30-ml portions of 10% hydrochloric acid and finally with 30 ml of water
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionHexane (30 ml) was added to the residue
  7. filtrationThe resulting white solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-959bd631dca745e49233fe48b4e77c1a
Source dataset
uspto-grants-2001_08
Patent number
US06278002B1

Reaction notes

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