Acetaldehyde → Benzyl 6-(1-hydroxyethyl)-3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 2058690Notes

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+].[CH:33](=[O:35])[CH3:34]>>[OH:35][CH:33]([CH:11]1[C:10](=[O:14])[N:9]2[CH:12]1[CH2:13][C:7]([O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])=[C:8]2[C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH3:34]

Participants

Reactant 3

HCID 177Acetaldehyde

HCID 2724682Lithium diisopropylamide

HCID 15136300Benzyl 3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Product 1

HCID 20549299Benzyl 6-(1-hydroxyethyl)-3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

Procedure

Benzyl 3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate is reacted with lithium diisopropylamide and acetaldehyde as described in Example 19 to provide benzyl 6-(1-hydroxyethyl)-3-(2-azidoethyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

Sources & evidence

ORD record: ord-bcdaa884ca8843ca8d1920d51a85dc05
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04318912

Reaction notes

Loading…