2-(2-Formamidothiazol-4-yl)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetic acid → 7-[2-(2-formamidothiazol-4-yl)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255788Notes

Reaction equation

HRID 255788 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]([OH:12])=O)[N:8]=1)=[O:2].[NH2:26][CH:27]1[C:47](=[O:48])[N:29]2[C:30]([C:44]([OH:46])=[O:45])=[C:31]([CH2:34][S:35][C:36]3[N:40]([CH2:41][CH:42]=[CH2:43])[N:39]=[N:38][N:37]=3)[CH2:32][S:33][C@H:28]12>>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]([NH:26][CH:27]2[C:47](=[O:48])[N:29]3[C:30]([C:44]([OH:46])=[O:45])=[C:31]([CH2:34][S:35][C:36]4[N:40]([CH2:41][CH:42]=[CH2:43])[N:39]=[N:38][N:37]=4)[CH2:32][S:33][C@H:28]23)=[O:12])[N:8]=1)=[O:2]

Participants

3

Reactant 2

HCID 540266432-(2-Formamidothiazol-4-yl)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetic acidHCID 704326537-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317153197-[2-(2-formamidothiazol-4-yl)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acidYield 33.9%

Procedure

2-(2-Formamidothiazol-4-yl)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetic acid (syn isomer, 1.86 g.) and 7-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (1.77 g.) were treated in similar manner to that of Example 20-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(3-tert-butoxycarbonylaminopropoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.2 g.).

Sources & evidence

ORD record
ord-3a0b868f80c54969a07075253bfe85ad
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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