Water → HCID 67796403, compound

HRID 1196194Notes

Reaction equation

HRID 1196194 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-2azetidinone (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. Filtration and concentration of the filtrate in vacuo gave an oily residue, which was crystallized from a mixture of cyclohexane and ethyl acetate to 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. filtrationFiltration and concentration of the filtrate in vacuo
  7. customgave an oily residue, which
  8. customwas crystallized from a mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-71117fd3208b4bb9b318100618c2095c
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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