Triethylamine → HCID 56980812, compound

HRID 1982106Notes

Reaction equation

HRID 1982106 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:8][C:9]([CH2:11][N:12]2[CH2:15][CH:14]([NH2:16])[C:13]2=[O:17])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:24]([CH2:31][C:32](Cl)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C1COCC1.O>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][C:9]([CH2:11][N:12]2[CH2:15][CH:14]([NH:16][C:32](=[O:33])[CH2:31][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:13]2=[O:17])=[O:10])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 57011224HCID 57011224, compound

Product 1

HCID 56980812HCID 56980812, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

For example, N-(diphenylmethoxycarbonylmethyl)-3-amino- 2-azetidinone is reacted in THF-water with phenoxyacetyl chloride in the presence of triethylamine to provide N-(diphenylmethoxycarbonylmethyl)-3-phenoxyacetamido-2-azetidinone. Treatment of the product with trifluoroacetic acid in the presence of anisole removes the diphenylmethyl ester group to provide the N-(carboxymethyl)azetidinone.

Sources & evidence

ORD record
ord-9aa7a89809fb462287407d8552ba46f9
Source dataset
uspto-grants-1986_06
Patent number
US04595532

Reaction notes

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