2-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid → HCID 178453833, compound

HRID 255797Notes

Reaction equation

[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[NH:15][N:14]=[N:13][CH:12]=3)[CH2:7][S:8][C@H:3]12.[CH:21]([NH:23][C:24]1[S:25][CH:26]=[C:27]([C:29](=[N:33][O:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:30](O)=[O:31])[N:28]=1)=[O:22]>>[CH:21]([NH:23][C:24]1[S:25][CH:26]=[C:27]([C:29](=[N:33][O:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:30]([NH:1][CH:2]2[C:19](=[O:20])[N:4]3[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]4[NH:15][N:14]=[N:13][CH:12]=4)[CH2:7][S:8][C@H:3]23)=[O:31])[N:28]=1)=[O:22]

Participants

Reactant 2

HCID 540828852-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid

HCID 178508102HCID 178508102, compound

Product 1

HCID 178453833HCID 178453833, compoundYield 67.7%

Procedure

7-Amino-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (1.7 g.) and 2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid (syn isomer, 2 g.) were treated in a similar manner to that of Example 20-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetamido]-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 2.4 g.).

Sources & evidence

ORD record: ord-7b3f84cc70a9469e9025dea60f867028
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04698337

Reaction notes

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