Dichloromethane → 7-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

HRID 1087260Notes

Reaction equation

HRID 1087260 reaction equation
ClCCl.C[C:5]([O:7][CH2:8][C:9]1[CH2:18][S:17][C@@H:12]2[C@H:13]([NH2:16])[C:14](=[O:15])[N:11]2[C:10]=1[C:19]([OH:21])=[O:20])=O.CS(O)(=O)=O.[OH-].[Na+]>CO>[NH2:16][CH:13]1[C:14](=[O:15])[N:11]2[C:10]([C:19]([OH:21])=[O:20])=[C:9]([CH2:8][O:7][CH3:5])[CH2:18][S:17][C@H:12]12

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 128330237-Amino-3-methoxymethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of dichloromethane were added 1.41 g of 7-ACA, 5.1 ml of methanesulfonic acid and 1.23 ml of methanol. The reaction was conducted at 0° C. for 6 hours. After completion of the reaction, the reaction mixture was poured into ice water. Then, the resultant mixture was adjusted to pH 3.5 with 10% aqueous sodium hydroxide to form a precipitate. The precipitate was collected by filtration, and then washed with water and dried to obtain the desired product, namely 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid. The amount of the desired product was 1.14 g. The yield of the desired product was 65%.

Workup

  1. customAfter completion of the reaction
  2. customto form a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-224468a1736347eca87e60686722b235
Source dataset
uspto-grants-1991_07
Patent number
US05034521

Reaction notes

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