Methanol → HCID 54010071, compound

HRID 1680083Notes

Reaction equation

HRID 1680083 reaction equation
[C:1]1([C:7]2[O:13][CH:12]3[CH:9]([C:10](=[O:41])[N:11]3[C@H:14]([C:31]([CH2:33][O:34]C(=O)C(F)(F)F)=[CH2:32])[C:15]([O:17][CH:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO>C(Cl)Cl>[C:1]1([C:7]2[O:13][CH:12]3[CH:9]([C:10](=[O:41])[N:11]3[C@H:14]([C:31]([CH2:33][OH:34])=[CH2:32])[C:15]([O:17][CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:16])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 54548486HCID 54548486, compound

Product 1

HCID 54010071HCID 54010071, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 240 mg of diphenylmethyl (2R)-2-(3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-3-trifluoroacetyloxymethyl-3-butenoate in 10 ml of a mixture (4:1) of methanol and methylene chloride is added 4.8 g of silica gel containing 10% water, and the mixture stirred for 30 minutes and filtered. The filter cake, silica gel, is washed several times with a mixture of methanol and methylene chloride. The combined filtrate and washings are evaporated under reduced pressure. The oily residue is chromatographed on 12 g of silica gel. Elution with a mixture (2:1) of benzene and ethyl acetate yields 106 mg of diphenylmethyl (2R)-2-(3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-3-hydroxymethyl-3-butenoate in 53% yield and 90 mg of the starting material in 35% recovery.

Workup

  1. filtrationfiltered
  2. washThe filter cake, silica gel, is washed several times
  3. additionwith a mixture of methanol and methylene chloride
  4. customThe combined filtrate and washings are evaporated under reduced pressure
  5. customThe oily residue is chromatographed on 12 g of silica gel
  6. washElution with a mixture (2:1) of benzene and ethyl acetate

Sources & evidence

ORD record
ord-b86fbd32bb03439dbf6bcd9b7715073a
Source dataset
uspto-grants-1981_06
Patent number
US04271295

Reaction notes

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