Ammonium Chloride → Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 371279

Reaction equation

HRID 371279 reaction equation
[C:1]1([CH3:29])[C:2]([S:7]([O:10][C:11]2[CH2:17][CH:16]3[N:13]([C:14](=[O:18])[CH2:15]3)[C:12]=2[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C([N-]C(C)C)(C)C.[Li+].[F:38][C:39]([F:43])([F:42])[CH:40]=[O:41].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[F:38][C:39]([F:43])([F:42])[CH:40]([CH:15]1[C:14](=[O:18])[N:13]2[CH:16]1[CH2:17][C:11]([O:10][S:7]([C:2]1[C:1]([CH3:29])=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:9])=[O:8])=[C:12]2[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[OH:41]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 65564TrifluoroacetaldehydeHCID 2724682Lithium diisopropylamideHCID 131712683Benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 131714283Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (41 mg) in anhydrous THF (0.5 ml) is added dropwise over 5 mins to a stirring solution of lithium diisopropylamide (from 15.5 μl of diisopropylamine and 70 μl of 1.6N BuLi) in anhydrous THF (1.5 ml) at -78°. The resulting solution is stirred under a N2 atm at -78° for 10 mins and then trifluoroacetaldehyde (50 mg) is added all at once. After 1 more min, saturated aqueous NH4Cl solution (1.5 ml) is added and the mixture is allowed to warm to room temperature. The mixture is diluted with EtOAc (20 ml), washed with water and brine, dried with MgSO4, filtered, and evaporated in vacuo. The benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washwashed with water and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-111f03d423fb4d3d9a0c6e83c4fafd9e
Source dataset
uspto-grants-1985_07
Patent number
US04530841

Linked notes

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