4-Toluenesulfonyl chloride → HCID 18633338, compound

HRID 232122Notes

Reaction equation

HRID 232122 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[C@H:11]([CH2:17][CH2:18][OH:19])[O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:29](Cl)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C@H:11]([CH2:17][CH2:18][O:19][S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[O:10][C:9]1([CH3:20])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 14649527HCID 14649527, compound

Product 1

HCID 18633338HCID 18633338, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

200 mg of the compound obtained in Example 10 was dissolved in 2 ml of dry methylene chloride, and 115 μl of triethylamine and 152 mg of tosyl chloride were added thereto. The mixture was stirred at room temperature overnight. Then, 115 μl of triethylamine was further added, and the mixture was reacted at room temperature and then evaporated to dryness under reduced pressure. A solution mixture of benzene/ethyl acetate (30/1) was added to the residue. After filtering insolubles off, the filtrate was purified by silica gel column chromatography to obtain 281 mg of (4S,5S)-3-tert-butyloxycarbonyl-2,2-dimethyl-5-(2-p-toluenesulfonyloxyethyl)-4-isobutyloxazolidine as a syrup.

Workup

  1. customthe mixture was reacted at room temperature
  2. customevaporated to dryness under reduced pressure
  3. additionA solution mixture of benzene/ethyl acetate (30/1)
  4. additionwas added to the residue
  5. filtrationAfter filtering insolubles off, the filtrate
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-59d2dfbb57674887985a9207315dbd9a
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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