Hydrochloric Acid → HCID 131710767, compound

HRID 2398145Notes

Reaction equation

HRID 2398145 reaction equation
C(CC(O)=O)C.[C:7]([O:10][CH2:11][C:12]1[CH2:13][S:14][C@@H:15]2[C@H:22]([NH:23][C:24](=[O:34])[C:25](=[N:32][OH:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:21](=[O:35])[N:16]2[C:17]=1[C:18]([OH:20])=[O:19])(=[O:9])[CH3:8].[Cl:36][CH2:37][CH2:38][N:39]=[C:40]=[O:41].Cl.P([O-])([O-])([O-])=O>CN(C)C=O.C(N(CC)CC)C>[C:7]([O:10][CH2:11][C:12]1[CH2:13][S:14][C@@H:15]2[C@H:22]([NH:23][C:24](=[O:34])[C:25](=[N:32][O:33][C:40](=[O:41])[NH:39][CH2:38][CH2:37][Cl:36])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:21](=[O:35])[N:16]2[C:17]=1[C:18]([OH:20])=[O:19])(=[O:9])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 160352-Chloroethyl isocyanateHCID 131710766HCID 131710766, compound

Product 1

HCID 131710767HCID 131710767, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-acetoxymethyl -7β-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylic acid ethyl acetate solvate (syn-isomer) (1.0 g.) in dimethylformamide (21 ml.) containing triethylamine (0.425 g) was added 2-chloroethylisocyanate (0.274 g.) and the mixture was stirred at room temperature for one hour. The reaction mixture was acidified (2N hydrochloric acid) and extracted with ethyl acetate. The extracts were combined and extracted with saturated aqueous sodium bicarbonate. The combined aqueous extracts were acidified (2N-hydrochloric acid) and extracted with ethyl acetate, dried, concentrated and added dropwise to petroleum with vigorous stirring. The precipitated solid was filtered, dissolved in ethyl acetate (10 ml.) and added dropwise to petroleum (300 ml.). The precipitate was filtered and dried giving the title acid (0.76 g; 74%), [α]D + 28° (c 1.0 DMSO), λmax. (pH 6 phosphate buffer) 257.5 nm. (ε 20,780), νmax. (Nujol) 3270 (NH), 1780 (β-lactam), 1660 and 1520 cm.-1 (amide), τ (DMSO-d6) values include -0.10 (doublet, J 8 Hz; NH), 6.2-6.7 (multiplet; C-2 CH2 + -CH2CH2Cl), 7.95 (singlet; OCOCH3).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionextracted with saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated
  6. additionadded dropwise to petroleum with vigorous stirring
  7. filtrationThe precipitated solid was filtered
  8. dissolutiondissolved in ethyl acetate (10 ml.)
  9. additionadded dropwise to petroleum (300 ml.)
  10. filtrationThe precipitate was filtered
  11. customdried
  12. customgiving the title acid (0.76 g; 74%), [α]D + 28° (c 1.0 DMSO), λmax

Sources & evidence

ORD record
ord-33b1bc8540284826afabfabd49155003
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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