Diazoethane → HCID 178474225, compound

HRID 258653

Reaction equation

HRID 258653 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:28])[C@@H:15]([NH:16][C:17](=[O:27])[CH2:18][C:19]3[CH:24]=[CH:23][NH:22][C:21](=[N:25][OH:26])[CH:20]=3)[C@H:12]2[S:11][CH2:10][C:9]=1[CH2:29][O:30][C:31](=[O:33])[CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH:36][CH3:37])=[N-]>O1CCCC1.CCOCC>[C:1]([O:5][C:6]([C:8]1[N:13]2[C:14](=[O:28])[C@@H:15]([NH:16][C:17](=[O:27])[CH2:18][C:19]3[CH:24]=[CH:23][NH:22][C:21](=[N:25][O:26][CH2:36][CH3:37])[CH:20]=3)[C@H:12]2[S:11][CH2:10][C:9]=1[CH2:29][O:30][C:31](=[O:33])[CH3:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 70695DiazoethaneHCID 178475882HCID 178475882, compound

Product 1

HCID 178474225HCID 178474225, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butyl-3-acetoxymethyl-7β-(2-hydroxyiminopyrid-4-ylacetamido)-ceph-3-em-4-carboxylate (syn-isomer) (1.15 g) in tetrahydrofuran (20 ml) was treated with an excess of diazoethane at 20° for 40 minutes. The mixture was diluted with ether, washed with water and extracted with 2 N-hydrochloric acid. The aqueous extract was neutralised with saturated sodium bicarbonate solution and extracted with ethyl acetate. Evaporation of the dried organic extract offered the title ester as a foam (0.84 g, 69%), [α]D + 47° (c 0.84, DMSO), λmax. (EtOH) 259 nm (ε 15,450), νmax. (Nujol) 3300 (NH), 1788 (β-lactam), 1740 (OAc), 1724 (CO2R), 1678 and 1540 cm.-1 (CONH), τ (d6 -DMSO) values include 0.12 (d, J 8 Hz; NH), 1.26 and 2.42 (multiplets; aromatic protons), 5.69 (q, J 7 Hz, OCH2CH 3), 7.93 (s; OCOCH3), 8.50 (s; (CH3)3) and 8.69 (t, J 7 Hz; OCH2CH3).

Workup

  1. washwashed with water
  2. extractionextracted with 2 N-hydrochloric acid
  3. extractionThe aqueous extract
  4. extractionextracted with ethyl acetate
  5. customEvaporation of the dried
  6. extractionorganic extract
  7. customthe title ester as a foam (0.84 g, 69%), [α]D + 47° (c 0.84, DMSO), λmax

Sources & evidence

ORD record
ord-b454034f25ec4cf7be54b8a9521ab830
Source dataset
uspto-grants-1977_07
Patent number
US04033950

Linked notes

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