Hydrochloric Acid → HCID 69963575, compound

HRID 1605396Notes

Reaction equation

HRID 1605396 reaction equation
CC([O:4][CH2:5][C:6]1[CH2:23][S:22][C@@H:9]2[C@H:10]([NH:13][C:14]([CH2:16][C:17]3[S:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:24]([OH:26])=[O:25])=O.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C.Cl>O>[OH:4][CH2:5][C:6]1[CH2:23][S:22][C@@H:9]2[CH:10]([NH:13][C:14](=[O:15])[CH2:16][C:17]3[S:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:12])[N:8]2[C:7]=1[C:24]([OH:26])=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6024CephalothinHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 69963575HCID 69963575, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

This substance was prepared according to German Offenlegungsschrift No. 2,103,014 as follows. A suspension of 8.0 g of cephalothin (1), available semi-synthetically, in 120 ml. of H2O treated with 8.6 g of K2CO3 and the resulting solution was stirred at 36° for 4.25 hours, then at 30° for 18 hours. The resulting mixture was layered with 500 ml of ethyl acetate and a solution of 10.0 ml of conc. HCl in 50 ml of H2O was added. The ethyl acetate was dried (MgSO4) and removed in vacuo in yield 3.84 g (54%) of 3-hydroxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid, mp 138°-145° d. Crystallization from ethyl acetate yielded material, mp 149°-151° d (lit. mp 151.5°-152° d); ir (nujol mull): 3600-2400 (carboxyl -OH), 3450 (amide N-H), 1790 (β-lactam C=O), 1745 (acid C=O), 1650 (amide C=O), and 1510 ("amide II" band) cm-1.

Workup

  1. customThis substance was prepared
  2. waitat 30° for 18 hours
  3. dry with materialThe ethyl acetate was dried (MgSO4)
  4. customremoved in vacuo in yield 3.84 g (54%) of 3-hydroxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid
  5. customCrystallization from ethyl acetate yielded material, mp 149°-151°

Sources & evidence

ORD record
ord-e9dfb8d9452944f8abb3c0ef9b5ec75f
Source dataset
uspto-grants-1976_04
Patent number
US03950329

Reaction notes

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