Triethylamine → HCID 12239785, compound

HRID 2083799Notes

Reaction equation

HRID 2083799 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:21]([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:22]>C(Cl)Cl>[C:21](=[O:22])([O:23][CH2:24][CH:25]([CH3:27])[CH3:26])[O:11][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 12239785HCID 12239785, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

One millimole of t-butoxycarbonyl-glycine in 10 ml methylene chloride at 0° is treated successively with one millimole each of triethylamine and isobutyl chloroformate, forming N-(t-butoxycarbonyl)glycyl i-butyl carbonate. To this solution at -78° is added p-nitrobenzyl 5-methoxymethyl 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-nitrobenzyl 7-t-butoxycarbonylamino-3-methoxymethyl decephalosporanate, which may be purified if desired by chromatography on silica gel, eluting with 4:1 chloroform-ethyl acetate.

Sources & evidence

ORD record
ord-0cd61d0ced6a45f1885b4b653babfebf
Source dataset
uspto-grants-1978_04
Patent number
US04086423

Reaction notes

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