Acetic Acid → HCID 131711546, compound

HRID 971417Notes

Reaction equation

HRID 971417 reaction equation
[N+](=[CH:3][C:4]([CH:6]1[O:12][CH:11]2[C:8]([C:34](=[O:42])[CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:9](=[O:33])[N:10]2[C:13](=[C:30]([CH3:32])[CH3:31])[C:14]([O:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[NH:7]1)=[O:5])=[N-].B(F)(F)F.CCOCC.[C:52]([OH:55])(=[O:54])[CH3:53]>>[C:52]([O:55][CH2:3][C:4]([CH:6]1[O:12][CH:11]2[C:8]([C:34](=[O:42])[CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:9](=[O:33])[N:10]2[C:13](=[C:30]([CH3:31])[CH3:32])[C:14]([O:16][CH:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[NH:7]1)=[O:5])(=[O:54])[CH3:53]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 131711544HCID 131711544, compound

Product 1

HCID 131711546HCID 131711546, compoundYield 30%

Procedure

To a solution of 200 mg of diphenylmethyl α-(3ξ-diazoacetyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 2 ml of acetic acid is added 0.045 ml of boron trifluoride etherate. After the termination of gas evolution, the reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is washed with water, an aqueous solution of sodium hydrogencarbonate and then water, dried on sodium sulfate and evaporated. The residue (205 mg) is purified by thin-layer chromatography to yield 65 mg of diphenylmethyl α-(3ξ-acetoxyacetyl-2-phenylacetyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]heptan-6-yl)-α-isopropylideneacetate in 30% yield.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materialan aqueous solution of sodium hydrogencarbonate and then water, dried on sodium sulfate
  4. customevaporated
  5. customThe residue (205 mg) is purified by thin-layer chromatography

Sources & evidence

ORD record
ord-fbc2223ea26841368a3d9c3811c2005b
Source dataset
uspto-grants-1979_07
Patent number
US04159984

Reaction notes

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