Dichloromethane → Benzhydryl (E)-(2S,3S,5R)-3-methyl-3-(2-pyridin-2-yl-vinyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 263749Notes

Reaction equation

HRID 263749 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH:8]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:28]([C@:30]1(C)[S:36][C@H:35]2[N:32]([C:33](=[O:37])[CH2:34]2)[C@H:31]1[C:38]([O:40][CH:41]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])=O.C(Cl)Cl>C(OCC)C>[CH3:28][C@@:30]1(/[CH:8]=[CH:7]/[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[S:36][C@H:35]2[N:32]([C:33](=[O:37])[CH2:34]2)[C@H:31]1[C:38]([O:40][CH:41]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 10762402benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateHCID 19038912(2-Picolyl)methylene-triphenylphosphorane

Product 1

HCID 10623688Benzhydryl (E)-(2S,3S,5R)-3-methyl-3-(2-pyridin-2-yl-vinyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 353 mg (1.0 mmol) of (2-picolyl)methylene-triphenylphosphorane and 381 mg (1.00 mmol) of benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-aza-bicyclo-[3.2.0]heptane-2-carboxylate in 10 ml of diethyl ether was stirred at room temperature under argon for 2 hours. The mixture was treated with 10 ml of methylene chloride, insoluble material was removed by suction filtration and the filtrate was concentrated. The residue remaining behind was chromatographed over silica gel (particle size 0.040-0.063 mm) with methylene chloride:ethyl acetate (95:5) as the eluent. Yield: 128 mg (28%) of a colorless foam MS: (M·) 456 IR (KBr): 1779, 1747, 1634, 1291, 988 cm-1

Workup

  1. customwas removed by suction filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue remaining behind was chromatographed over silica gel (particle size 0.040-0.063 mm) with methylene chloride:ethyl acetate (95:5) as the eluent

Sources & evidence

ORD record
ord-b26658d52e644162a6c53180ac1a334a
Source dataset
uspto-grants-1997_07
Patent number
US05644053

Reaction notes

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