Oxalyl chloride → HCID 53756007, compound

HRID 1380288Notes

Reaction equation

[CH3:1][O:2][N:3]=[C:4]([C:8]1[S:12][C:11]2[CH:13]=[C:14]([Cl:16])[S:15][C:10]=2[CH:9]=1)[C:5](O)=[O:6].C(Cl)(=O)C([Cl:20])=O>>[CH3:1][O:2][N:3]=[C:4]([C:8]1[S:12][C:11]2[CH:13]=[C:14]([Cl:16])[S:15][C:10]=2[CH:9]=1)[C:5]([Cl:20])=[O:6]

Participants

Reactant 2

HCID 65578Oxalyl chloride

HCID 54039760HCID 54039760, compound

Product 1

HCID 53756007HCID 53756007, compound

Procedure

Following the procedure of Example 1, 827 mg of α-methoxyimino-α-(5-chlorothieno[3,2-b]thien-2-yl)-acetic acid from Preparation 2 was reacted with oxalyl chloride to provide α-methoxyimino-α-(5-chlorothieno[3,2-b]thien-2-yl)acetyl chloride which was reacted with 642 mg of 7-amino-3-methyl-3-cephem-4-carboxylic acid silylated with 2.31 g of BSTFA. The reaction afforded 1.1 g of 7-[α-methoxyimino-α-(5-chlorothieno[3,2-b]thien-2-yl)acetamido]-3-methyl-3-cephem-4-carboxylic acid. The thienothienyl oxime was reacted with 544 mg of zinc dust in formic acid and methanol to provide 1.1 g of 7-(5-chlorothieno[3,2-b]thien-2-yl)glycylamido-3-methyl-3-cephem-4-carboxylic acid. Reverse phase high performance chromatography provided

Workup

customfrom Preparation 2

Sources & evidence

ORD record: ord-a923a693fb1a44f098f4f38496011c29
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04581352

Reaction notes

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