Phosphorus tribromide → 3-Bromo-7-cyanomethylthioacetamido-3-cephem-4-Carboxylic Acid Benzhydryl Ester

HRID 1287606Notes

Reaction equation

HRID 1287606 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:32])[CH:24]([NH:25][C:26](=[S:31])[CH2:27][CH2:28][C:29]#[N:30])[C@H:21]2[S:20][CH2:19][C:18]=1O)=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:35]>>[CH:1]([O:14][C:15]([C:17]1[N:22]2[C:23](=[O:32])[CH:24]([NH:25][C:26](=[S:31])[CH2:27][CH2:28][C:29]#[N:30])[C@H:21]2[S:20][CH2:19][C:18]=1[Br:35])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24614Phosphorus tribromideHCID 1317104807-Cyanomethylthioacetamido-3-cephem-3-ol-4-carboxylic acid Benzhydryl Ester

Product 1

HCID 1317104843-Bromo-7-cyanomethylthioacetamido-3-cephem-4-Carboxylic Acid Benzhydryl Ester

Procedure

The desired product is prepared from 7-cyanomethylthioacetamido-3-cephem-3-ol-4-carboxylic acid benzhydryl ester using the procedure described in Example 5, but replacing phosphorus trichloride with phosphorus tribromide.

Sources & evidence

ORD record
ord-00373c9006e94f5584bd87cd98e6f6ce
Source dataset
uspto-grants-1976_10
Patent number
US03985746

Reaction notes

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