Butanethiol → (3S, 4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-[(butylthio)carbonylmethyl]-2-azetidinone

HRID 342281Notes

Reaction equation

HRID 342281 reaction equation
[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([OH:18])=O)[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:20]([SH:24])[CH2:21][CH2:22][CH3:23].C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([CH2:15][C:16]([S:24][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])[NH:13][C:12]1=[O:19])[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8012ButanethiolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 10859145(3S,4R)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-oxoazetidine

Product 1

HCID 88720775(3S, 4R)-3-[(R)-1-t-Butyldimethylsilyloxyethyl]-4-[(butylthio)carbonylmethyl]-2-azetidinoneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

542 mg (1.89 mmole) of (3S, 4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-carboxymethyl-2-azetidinone, 212 mg (2.36 mmole) of butyl mercaptan, 381 mg (3.77 mmole) of triethylamine and 1.04 g (3.78 mmole) of diphenylphosphoryl azide were dissolved in 10 ml of N,N-dimethylformamide and the solution was allowed to stand overnight at room temperature. After dilution with ethyl acetate, the mixture was washed with water several times and then dried. The solvent was distilled off and the residue (1.25 g) was purified by column chromatography through 23 g of silical gel, eluted with mixtures of hexane and ethyl acetate in volume ratios ranging from 4:1 to 2:1, to give 649 mg (yield 96%) of the title product. Recrystallization from hexane gave colourless needles, melting at 56.5°-57° C.

Workup

  1. washAfter dilution with ethyl acetate, the mixture was washed with water several times
  2. customdried
  3. distillationThe solvent was distilled off
  4. customthe residue (1.25 g) was purified by column chromatography through 23 g of silical gel
  5. washeluted with mixtures of hexane and ethyl acetate in volume ratios

Sources & evidence

ORD record
ord-20eaf29e754941d294f2555a65038ea2
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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