Acetic Acid → Diphenylmethyl 3-acetoxymethyl-7beta-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylate

HRID 1707191Notes

Reaction equation

HRID 1707191 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:28])[C:19](=[N:26][OH:27])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15](=[O:29])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].[C:30]1([C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N+]=[N-])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O)(=O)C>O1CCCC1>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:28])[C:19](=[N:26][OH:27])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:15](=[O:29])[N:10]2[C:11]=1[C:12]([O:14][CH:36]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 88767746HCID 88767746, compound

Product 1

HCID 131710762Diphenylmethyl 3-acetoxymethyl-7beta-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-acetoxymethyl-7β-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylic acid (syn-isomer)(2.0 g) in tetrahydrofuran (50 ml.) maintained at 37° was added portionwise a solution of diphenyldiazomethane in petroleum (b.p. 60°-80°) until the purple colour persisted for one hour. After addition of acetic acid to destroy excess diphenyldiazomethane, the solution was evaporated to dryness, taken up in ethyl acetate, then washed with sodium bicarbonate, and brine, dried and evaporated. The residue was triturated with petroleum spirit, and the resulting solid filtered and dried to give diphenylmethyl 3-acetoxymethyl-7β-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylate (syn-isomer) (1.93 g 69%), [α]D +24° (c 1, DMSO), λmax. (EtOH) 253 nm (ε 16,150), νmax. (CHBr3) 3610 (OH), 1796 cm.-1 (β-lactam), τ (DMSO-d6) values include 0.27 (doublet, J 9 Hz; NH), 8.03 (singlet; OCOCH 3).

Workup

  1. customto destroy excess diphenyldiazomethane
  2. customthe solution was evaporated to dryness
  3. washwashed with sodium bicarbonate, and brine
  4. customdried
  5. customevaporated
  6. customThe residue was triturated with petroleum spirit
  7. filtrationthe resulting solid filtered
  8. customdried

Sources & evidence

ORD record
ord-f49f9af090c74cecb7abefc9c02e374b
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

Loading…