Water → HCID 67796403, compound

HRID 1033462Notes

Reaction equation

HRID 1033462 reaction equation
O[C:2]([C@H:5]1[N:8]([CH:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[CH3:30])([CH3:4])[CH3:3].S(Cl)(Cl)=O.N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[CH3:4][C:2]([C@H:5]1[N:8]([CH:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C:7](=[O:28])[C@@H:6]1[C@H:29]([O:31][C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])[CH3:30])=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 67796529(3S,4S)-4-(1-hydroxy-1-methylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2azetidinone

Product 1

HCID 67796403HCID 67796403, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (3S,4S)-4-(1-hydroxy-1-methylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (30 g) in dry toluene (350 ml) was treated with thionyl chloride (9.0 g) at 20°-30° C. for 5 hours in the presence of pyridine (10 ml). Water (100 ml) was added to quench the reaction at 10°-25° C. The organic layer was separated, washed with water and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo to give an oily residue, which was crystallized from a mixture of cyclohexane and ethyl acetate yield (3S,4S)-4-(1-methylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone. m.p., 117°-118° C.

Workup

  1. customto quench
  2. customthe reaction at 10°-25° C
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customto give an oily residue, which
  9. customwas crystallized from a mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-caea5ae1736847ecbd27e5ac3a07e291
Source dataset
uspto-grants-1994_05
Patent number
US05310897

Reaction notes

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