(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid → HCID 131714078, compound

HRID 2412412Notes

Reaction equation

HRID 2412412 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:8]1[C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[S:10][CH:9]=1)[C:5]([OH:7])=O.[NH2:18][CH:19]1[C:30](=[O:31])[N:21]2[C:22]([C:27]([OH:29])=[O:28])=[C:23]([CH3:26])[CH2:24][S:25][C@H:20]12>>[CH3:1][O:2][N:3]=[C:4]([C:8]1[C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[S:10][CH:9]=1)[C:5]([NH:18][CH:19]1[C:30](=[O:31])[N:21]2[C:22]([C:27]([OH:29])=[O:28])=[C:23]([CH3:26])[CH2:24][S:25][C@H:20]12)=[O:7]

Participants

3

Reactant 2

HCID 13475828(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 541976636-Chloro-α-(methoxyimino)benzo[b]thiophene-3-acetic acid

Product 1

HCID 131714078HCID 131714078, compoundYield 7,959.2%

Procedure

Following the general procedure of Example 36, 2.8 g (10.39 mM) of α-methoxyimino-α-(6-chloro-3-benzothienyl)acetic acid were converted to the acid chloride and reacted with 2.33 g (10.91 mM) of 7-amino-3-methyl-3-cephem-4-carboxylic acid to provide 385 g (80% yield) of 7-[α-methoxyimino-α-(6-chloro-3-benzothienyl)acetamido]-3-methyl-3-cephem-4-carboxylic acid. NMR (CDCl3): δ 2.02 and 2.21 (two s, 3H); δ 3.1-3.85 (m, 2H); δ 4.01 (s, 3H); δ 5.06 (d, 1H); δ 5.86 (dd, 1H); δ 7.2-7.8 (m, 4H); δ 8.3-8.7 (m, 2H).

Sources & evidence

ORD record
ord-770f6787723d49738037c91aeb1cc956
Source dataset
uspto-grants-1985_01
Patent number
US04492693

Reaction notes

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