Triethylamine → HCID 20357884, compound

HRID 2083801Notes

Reaction equation

HRID 2083801 reaction equation
[CH3:1][O:2][CH:3]([C:13]([OH:15])=[O:14])[NH:4][C:5](=[O:12])[CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25]>C(Cl)Cl>[C:24](=[O:25])([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])[O:14][C:13](=[O:15])[CH:3]([O:2][CH3:1])[NH:4][C:5](=[O:12])[CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 20357807HCID 20357807, compound

Product 1

HCID 20357884HCID 20357884, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

One millimole of α-methoxy-N-(2-thienylacetyl)glycine in 10 ml methylene chloride at 0° is treated successively with one millimole each of triethylamine and isobutyl chloroformate, forming α-methoxy-N-(2-thienylacetyl)glycyl i-butyl carbonate. To this solution at -78° is added p-methoxybenzyl-5-N,N-di(p-methoxybenzyl)aminocarbonyloxymethyl 6H-1,3-thiazine-4-carboxylate, and then a second millimole of triethylamine. The reaction mixture is allowed to warm to room temperature over one hour, and kept at 25° one hour. The mixture is then washed successively with aqueous pH 2 buffer, water, and aqueous bicarbonate, dried with MgSO4, filtered and evaporated, affording p-methoxybenzyl 7-methoxy-7-(2-thienylacetamido)-3-N,N-di(p-methoxybenzyl)aminocarbonyloxymethyl decephalosporanate, which may be purified if desired by chromatography on silica gel, eluting with 4:1 chloroformethyl acetate.

Sources & evidence

ORD record
ord-656887cdfb414927a85ae9f007225b14
Source dataset
uspto-grants-1978_04
Patent number
US04086423

Reaction notes

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