Diazomethane → HCID 131711461, compound

HRID 614644Notes

Reaction equation

HRID 614644 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:25](=[O:26])[N:12]2[C:13]([C:22]([OH:24])=[O:23])=[C:14]([CH2:17][O:18][C:19](=[O:21])[NH2:20])[CH2:15][S:16][C@H:11]12)=[O:8].[N+](=[CH2:29])=[N-]>C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:25](=[O:26])[N:12]2[C:13]([C:22]([O:24][CH3:29])=[O:23])=[C:14]([CH2:17][O:18][C:19](=[O:21])[NH2:20])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 70567479HCID 70567479, compound

Product 1

HCID 131711461HCID 131711461, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-(2-(2-Thienyl)acetamido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (50 milligrams) in ethanol was reacted with excess diazomethane. After five minutes the excess diazomethane was evaporated and the desired methyl ester crystallized with ethanol, then with chloroform, and with acetone. Nine milligrams of the desired 7-(2-(2-thienyl)acetamido)-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid, methyl ester were obtained, m.p., 212°-214° C.

Workup

  1. customAfter five minutes the excess diazomethane was evaporated
  2. customthe desired methyl ester crystallized with ethanol

Sources & evidence

ORD record
ord-3d532f4c9fc94cedad2fed1d18c63949
Source dataset
uspto-grants-1979_03
Patent number
US04145538

Reaction notes

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