Hydrogen Sulfide → HCID 88833334, compound

HRID 1576062Notes

Reaction equation

HRID 1576062 reaction equation
[N+](=[CH:3][C:4]1[CH2:5][S:6][C@@H:7]2[C@H:27]([NH:28][C:29](=[O:36])[CH2:30][C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[C:26](=[O:37])[N:8]2[C:9]=1[C:10]([O:12][CH:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[N-].[SH2:38]>ClCCl>[SH:38][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[C@H:27]([NH:28][C:29](=[O:36])[CH2:30][C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[C:26](=[O:37])[N:8]2[C:9]=1[C:10]([O:12][CH:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:11]

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 131710446HCID 131710446, compound

Product 1

HCID 88833334HCID 88833334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of benzhydryl 3-diazomethyl-7β-(2-thienylacetamido)-ceph-3-em-4-carboxylate (9.0 × 10-4 mole), prepared by the process described in Example 2, in 5 ml. dichloromethane solvent is stirred at room temperature while a slow stream of hydrogen sulfide gas is bubbled in. The excess gas and solvent is removed in vacuo and the residue chromatographed over silica gel with chloroform:acetone (10:1) to give benzhydryl 3-mercaptomethyl-7β-(2-thienylacetamido)-ceph-3-em-4-carboxylate.

Workup

  1. customis bubbled in
  2. customThe excess gas and solvent is removed in vacuo
  3. customthe residue chromatographed over silica gel with chloroform:acetone (10:1)

Sources & evidence

ORD record
ord-410690266ece4e8ea8612e7fb38ab134
Source dataset
uspto-grants-1976_09
Patent number
US03979384

Reaction notes

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