Dichloromethane → HCID 54464663, compound

HRID 1723460Notes

Reaction equation

HRID 1723460 reaction equation
[Si]([N:8]1[C@H:11](O[Si](C)(C)C)[C@@H:10]([C@H:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH3:18])[C:9]1=[O:27])(C(C)(C)C)(C)C.C(Cl)Cl.CN(C1C=CC=CN=1)C.C(OC(=O)C)(=O)C>CCCCCC>[Si:20]([O:19][C@@H:17]([CH:10]1[CH2:11][NH:8][C:9]1=[O:27])[CH3:18])([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 54204585HCID 54204585, compound

Product 1

HCID 54464663HCID 54464663, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

There was dissolved 1 g of (3R,4R)-1-tert-butyldimethylsilyl-3-[(R)-1-tert-butyldimethylsilyloxyethyl]-4-trimethylsilyloxyazetidin-2-one into 10 ml of methylene chloride, thereto 0.85 g of dimethylaminopyridine and 0.71 g of acetic anhydride were added and the mixture was reacted for one day at 0° C. After the reaction mixture was diluted with hexane and washed successively with 5% aqueous solution of NaHCO3, an aqueous solution of hydrochloric acid of pH 4 and saturated solution of salt, the resultant was dried with magnesium sulfate and the solvent was distilled away to give 0.85 of a liquid crude product. The obtained liquid was purified by a silica-gel column chromatography (hexane:ether=30:1) to give 0.40 g of (3R,4R)-4-acetoxy-1-tert-butyldimethylsilyl)-3-[(R)-1-tert-butyldimethylsilyloxyethyl)azetidin-2-one as a colorless liquid.

Workup

  1. customthe mixture was reacted for one day at 0° C
  2. washwashed successively with 5% aqueous solution of NaHCO3
  3. dry with materialan aqueous solution of hydrochloric acid of pH 4 and saturated solution of salt, the resultant was dried with magnesium sulfate
  4. distillationthe solvent was distilled away
  5. customto give 0.85 of a liquid crude product
  6. customThe obtained liquid was purified by a silica-gel column chromatography (hexane:ether=30:1)

Sources & evidence

ORD record
ord-548674b16fab474ca202fdf6c51ce6b6
Source dataset
uspto-grants-1989_08
Patent number
US04861877

Reaction notes

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