Methanethiol → HCID 70615406, compound

HRID 1763814Notes

Reaction equation

HRID 1763814 reaction equation
Br[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:18]([NH:19][C:20](=[O:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17](=[O:30])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10].[CH3:31][SH:32]>CN(C)C=O>[CH3:31][S:32][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:18]([NH:19][C:20](=[O:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17](=[O:30])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]([Cl:16])([Cl:15])[Cl:14])=[O:10]

Participants

4

Reactant 2

HCID 878MethanethiolHCID 70615973HCID 70615973, compound

Product 1

HCID 70615406HCID 70615406, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2,2-Trichloroethyl 3-bromomethyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate, 1β-oxide (11.48g, 20 mmole) was reacted with methanethiol as in Example D18(i) and the resulting solution in N,N-dimethylformamide used directly in a reduction step as described in Example D18(ii) to provide the solvated title compound as a pale-yellow foam (10.90 g,), [α]D + 37.5° (c, 1.25) λmax. 269 nm (E1cm1% 165) and 276 nm. (E1cm1% 160) inflexion at 263 nm (E1cm1% 151). The P.M.R. spectrum of this product closely resembled that of the product from Example D18(ii)

Sources & evidence

ORD record
ord-c1d3dd03d4e34b2eade7499b24cb5158
Source dataset
uspto-grants-1978_09
Patent number
US04113591

Reaction notes

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