Acetic Acid → HCID 86596178, compound

HRID 1271109Notes

Reaction equation

HRID 1271109 reaction equation
[NH2:1][C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:17][C@H:16]3[N:13]([C:14](=[O:28])[C@@H:15]3[C@H:18]([O:20][Si](CC)(CC)CC)[CH3:19])[C:12]=2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])=[CH:7][CH:6]=1)=[O:3].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C1COCC1>[NH2:1][C:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH2:17][C@H:16]3[N:13]([C:14](=[O:28])[C@@H:15]3[C@H:18]([OH:20])[CH3:19])[C:12]=2[C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:30])=[CH:9][CH:10]=1)=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11078149TBAF tetrahydrofuranHCID 86596176HCID 86596176, compound

Product 1

HCID 86596178HCID 86596178, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitrobenzyl (5R,6S)-3-{4-[(aminocarbonyl)oxy]phenyl}-6-{(1R)-1-[(triethylsilyl)oxy]ethyl}-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (110 mg) prepared in the above step in THF (1.9 ml) was added under ice cooling acetic acid (11 mg). Then 1M tetrabutylammonium fluoride/THF solution (0.19 ml) was dropped thereto and the mixture was stirred at the same temperature for 45 minutes. The residue prepared by the same manner as step a) of example 11 was purified by silica gel thin-layer chromatography (chloroform/acetone=2/1) to give 4-nitrobenzyl (5R,6S)-3-{4-[(aminocarbonyl)oxy]phenyl}-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (11 mg).

Workup

  1. additionwas added under ice
  2. customThe residue prepared by the same manner as step a) of example 11
  3. customwas purified by silica gel thin-layer chromatography (chloroform/acetone=2/1)

Sources & evidence

ORD record
ord-08e1f074873f4cc1b8426c748e1c32b9
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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