tert-butyl (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → t-Butyl 3-acetoxymethyl-7beta-(2-dichloroacetoxyimino-2-phenylacetamido)-ceph-3-em-4-carboxylate

HRID 1707176Notes

Reaction equation

HRID 1707176 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:20]([NH2:21])[C:19](=[O:22])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:3])[CH3:2].[Cl:23][CH:24]([Cl:39])[C:25]([O:27][N:28]=[C:29]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:30](Cl)=[O:31])=[O:26]>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:20]([NH:21][C:30](=[O:31])[C:29](=[N:28][O:27][C:25](=[O:26])[CH:24]([Cl:39])[Cl:23])[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:19](=[O:22])[N:10]2[C:11]=1[C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 15573427tert-butyl (6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateHCID 540574962-Dichloroacetoxyimino-2-phenylacetyl chloride

Product 1

HCID 131711799t-Butyl 3-acetoxymethyl-7beta-(2-dichloroacetoxyimino-2-phenylacetamido)-ceph-3-em-4-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of t-butyl 3-acetoxymethyl-7β-aminoceph-3-em-4-carboxylate (3.28 g) in ethyl acetate (25 ml.) was added a solution of 2-dichloroacetoxyimino-2-phenylacetyl chloride (syn-isomer) in ethyl acetate (25 ml.) dropwise with stirring. The solution became warm and a precipitate formed. After two hours, the solution was filtered, washed successively with 2 N-hydrochloric acid, water, and saturated sodium bicarbonate solution, dried, and evaporated to give a yellow foam which solidified on standing, and was triturated with petroleum spirit giving t-butyl 3-acetoxymethyl-7β-(2-dichloroacetoxyimino-2-phenylacetamido)-ceph-3-em-4-carboxylate (4.0 g; 70%), νmax. (CHBr3) 3420 (NH), 1796 (β-lactam), 1730 and 1230 (acetate), 1700 and 1512 cm-1 (CONH), τ (DMSO-d6) values include 2.1-2.5 (multiplet; aromatic protons), 2.98 (singlet; CHCl2), 7.6 (singlet; CH3CO), 8.5 (singlet; t-butyl ester).

Workup

  1. temperatureThe solution became warm
  2. customa precipitate formed
  3. filtrationthe solution was filtered
  4. washwashed successively with 2 N-hydrochloric acid, water, and saturated sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. customto give a yellow foam which
  8. customwas triturated with petroleum spirit

Sources & evidence

ORD record
ord-f47070b51d7e4b529dd50234777ad473
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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