HCID 131712248, compound → HCID 131712247, compound

HRID 1381366Notes

Reaction equation

HRID 1381366 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:38]1[N:42]=[C:41]([NH2:43])[S:40][N:39]=1)[C:5]([NH:7][CH:8]1[C:36](=[O:37])[N:10]2[C:11]([C:33]([OH:35])=[O:34])=[C:12]([CH2:15][S:16][C:17]3[N:21]([CH2:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)[N:20]=[N:19][N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6]>C(O)=O>[CH3:1][O:2][N:3]=[C:4]([C:38]1[N:42]=[C:41]([NH2:43])[S:40][N:39]=1)[C:5]([NH:7][CH:8]1[C:36](=[O:37])[N:10]2[C:11]([C:33]([OH:35])=[O:34])=[C:12]([CH2:15][S:16][C:17]3[N:21]([CH2:22][CH2:23][CH2:24][NH2:25])[N:20]=[N:19][N:18]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

3

Reactant 1

HCID 131712248HCID 131712248, compound

Product 1

HCID 131712247HCID 131712247, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[1-{3-(N-t-butoxycarbonylamino)propyl}-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (2.22 g) in formic acid (22 ml) was stirred for 2.5 hours at ambient temperature. The reaction mixture was post-treated in a conventional manner to give 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-[1-(3-aminopropyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.875 g), mp. 185° to 190° C. (dec.).

Workup

  1. additionThe reaction mixture was post-treated in a conventional manner

Sources & evidence

ORD record
ord-aa2f8c5394f84eb784b4e9ea1ea44cf4
Source dataset
uspto-grants-1986_04
Patent number
US04585872

Reaction notes

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