2-Thiopheneacetyl chloride → HCID 88806039, compound

HRID 1679190Notes

Reaction equation

HRID 1679190 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](Cl)=[O:8].[NH2:10][CH:11]1[C:26](=[O:27])[N:13]2[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[CH2:16][S:17][C@:12]12[S:28][CH3:29].C([O-])(O)=O.[Na+]>O.CC(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:10][CH:11]1[C:26](=[O:27])[N:13]2[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18][O:19][C:20](=[O:22])[CH3:21])[CH2:16][S:17][C@:12]12[S:28][CH3:29])=[O:8]

Participants

6

Reactant 3

HCID 1623622-Thiopheneacetyl chlorideHCID 516892Sodium BicarbonateHCID 88805992HCID 88805992, compound

Product 1

HCID 88806039HCID 88806039, compoundYield 33.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-Thienylacetyl chloride (28 μl, 0.209 mMol) is added to an ice-cold, stirring mixture of 7-amino-6-methylthio-3-acetoxymethyl-ceph-3-em-4-carboxylic acid (66.4 mg., 0.209 mMol) and NaHCO3 (35 mg., 0.418 mMol) in H2O (1.5 ml.) and acetone (3.0 ml.). After stirring for 30 mins. in the cold, the mixture is evaporated under reduced pressure to remove acetone. The aqueous residue is diluted with more H2O (4.5 ml). and extracted with three portions of Et2O. The aqueous phase is acidified to pH 2.5 with 10% HCl and extracted with three portions of EtOAc. The EtOAc solution is dried over MgSO4, filtered, and evaporated in vacuo to a solid (72 mg.). This material is extracted with φH to remove 2-thienylacetic acid and the residue recrystallized from CH3CN-Et2O to provide 7-(2-thienylacetamido)-6-methylthio-3-acetoxymethyl-ceph-3-em-4-carboxylic acid (31 mg.) as an off-white solid.

Workup

  1. stirringAfter stirring for 30 mins
  2. customin the cold, the mixture is evaporated under reduced pressure
  3. customto remove acetone
  4. additionThe aqueous residue is diluted with more H2O (4.5 ml)
  5. extractionand extracted with three portions of Et2O
  6. extractionextracted with three portions of EtOAc
  7. dry with materialThe EtOAc solution is dried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo to a solid (72 mg.)
  10. extractionThis material is extracted with φH
  11. customto remove 2-thienylacetic acid
  12. customthe residue recrystallized from CH3CN-Et2O

Sources & evidence

ORD record
ord-cd3923b0fdea4781a257d6bc916c7ed3
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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