Benzenesulfonyl chloride → HCID 13370423, compound

HRID 2412325Notes

Reaction equation

HRID 2412325 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][C@H:10]1[NH:13][C:12](=[O:14])[CH2:11]1.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[C:15]1([S:21]([O:8][CH2:9][C@H:10]2[NH:13][C:12](=[O:14])[CH2:11]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 10964424(4S)-4-(hydroxymethyl)azetidin-2-one

Product 1

HCID 13370423HCID 13370423, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (5.74 g, 56.8 mmol) was added by syringe to a solution of (S)-4-hydroxymethylazetidin-2-one (3.79 g, 37.5 mmol) and benzenesulfonylchloride (10.0 g, 56.8 mmol) in dry methylene chloride (38 ml) at 0° C. The resulting mixture was stirred at 0° C. for 4 hrs., then diluted with methylene chloride (100 ml), washed with water (50 ml) and brine (25 ml) and dried over magnesium sulfate. Solvents were removed in vacuo to give a brown gum which was chromatographed on silica gel (100 g) (ethylacetate) to yield 6.6 g (73%) of (S)-4-benzenesulfonyloxymethyl azetidin-2-one as a white solid, m.p. 102°-105° C.

Workup

  1. washwashed with water (50 ml) and brine (25 ml)
  2. dry with materialdried over magnesium sulfate
  3. customSolvents were removed in vacuo
  4. customto give a brown gum which
  5. customwas chromatographed on silica gel (100 g) (ethylacetate)

Sources & evidence

ORD record
ord-0a822a35fa6648c8be2eeeeba218e765
Source dataset
uspto-grants-1985_01
Patent number
US04491580

Reaction notes

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