Benzenepropanal → Benzyl 6-(3-phenyl-1-hydroxypropyl)-3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1493478Notes

Reaction equation

HRID 1493478 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH2:13][CH:12]2[N:9]([C:10](=[O:14])[CH2:11]2)[C:8]=1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=[N+:2]=[N-:3].C([N-]C(C)C)(C)C.[Li+].[C:33]1([CH2:39][CH2:40][CH:41]=[O:42])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[C:33]1([CH2:39][CH2:40][CH:41]([CH:11]2[C:10](=[O:14])[N:9]3[CH:12]2[CH2:13][C:7]([O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])=[C:8]3[C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[OH:42])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 7707BenzenepropanalHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 15136300Benzyl 3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 15136310Benzyl 6-(3-phenyl-1-hydroxypropyl)-3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (66 mg) in anhydrous THF (0.5 ml) is added dropwise over 5 mins to a stirring solution of lithium diisopropylamide (from 31 μl diisopropylamine and 140 μl 1.6N BuLi) in anhydrous THF (3.5 ml) at -78°. After stirring an additional 15 mins at -78° under N2, the solution is treated with 3-phenylpropionaldehyde (134 mg, 5 equivalents) in THF (0.5 ml). After 5 more mins at -78°, the solution is treated with saturated aqueous NH4Cl (3 ml) and allowed to warm to room temperature. The mixture is diluted with EtOAc (50 ml), washed with water (3×10 ml) and brine, dried with MgSO4, filtered, and evaporated in vacuo. The residue is chromatographed on silica gel to yield benzyl 6-(3-phenyl-1-hydroxypropyl)-3 -(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Workup

  1. washwashed with water (3×10 ml) and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-6fbcf1ab982e463299a4cf01e127ef02
Source dataset
uspto-grants-1991_06
Patent number
US05021566

Reaction notes

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