Methanol → HCID 70604422, compound

HRID 2164133Notes

Reaction equation

HRID 2164133 reaction equation
[CH3:1][S:2][CH:3]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[C:4]([NH:6][CH:7]1[C:22](=[O:23])[N:9]2[C:10](C(O)=O)=[C:11]([CH2:14]OC(=O)C)[CH2:12][S:13][C@H:8]12)=[O:5].[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH3:35][OH:36].[OH2:37]>>[CH3:1][S:2][CH:3]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[C:4]([NH:6][CH:7]1[C:22](=[O:23])[N:9]2[CH:10]=[C:11]([CH2:14][N+:29]3[CH:34]=[CH:33][C:32]([C:35]([O-:37])=[O:36])=[CH:31][CH:30]=3)[CH2:12][S:13][C@H:8]12)=[O:5]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1049PyridineHCID 70604746HCID 70604746, compound

Product 1

HCID 70604422HCID 70604422, compound

Procedure

7-[α-Methylthio(2-thienyl)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (1.0 g) was suspended in 10 ml of water, and 1 ml of pyridine was added. The mixture was stirred until the acid dissolved. The resulting solution (pH 5.9) was maintained at 35° C. for 3 days. After filtration, it was extracted four times with 10 ml of chloroform. The extract was extracted with a small amount of water, and the aqueous solution was allowed to flow through a column of an acetate-form Dowex 1 × 8 (100 to 200 mesh, 20 g). The column was washed with water, and the eluate obtained was lyophilized. The dried product obtained was treated with a small amount of methanol, filtered off and dried to afford the above final product.

Workup

  1. dissolutiondissolved
  2. filtrationAfter filtration, it
  3. extractionwas extracted four times with 10 ml of chloroform
  4. extractionThe extract was extracted with a small amount of water
  5. washThe column was washed with water
  6. customthe eluate obtained
  7. customThe dried product obtained
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-216c09c9af4d4d3a814a46da756ca76a
Source dataset
uspto-grants-1979_01
Patent number
US04137406

Reaction notes

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