Trichloroacetyl isocyanate → HCID 131710430, compound

HRID 1390403Notes

Reaction equation

HRID 1390403 reaction equation
[Cl:1][C:2]([Cl:9])([Cl:8])[C:3]([N:5]=[C:6]=[O:7])=[O:4].[OH:10][CH2:11][C:12]1[CH2:13][S:14][C@@H:15]2[C@H:35]([NH:36][C:37](=[O:44])[CH2:38][C:39]3[S:40][CH:41]=[CH:42][CH:43]=3)[C:34](=[O:45])[N:16]2[C:17]=1[C:18]([O:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CC(C)=O>[S:40]1[CH:41]=[CH:42][CH:43]=[C:39]1[CH2:38][C:37]([NH:36][C@@H:35]1[C:34](=[O:45])[N:16]2[C:17]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])=[C:12]([CH2:11][O:10][C:6](=[O:7])[NH:5][C:3](=[O:4])[C:2]([Cl:9])([Cl:8])[Cl:1])[CH2:13][S:14][C@H:15]12)=[O:44]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 390251HCID 390251, compound

Product 1

HCID 131710430HCID 131710430, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Trichloroacetyl isocyanate (13.2 g, 70 mmole) was added to a stirred suspension of diphenylmethyl (6R,7R)-3-hydroxymethyl-7-(thien-2-ylacetamido)ceph-3-em-4 carboxylate (26.0 g, 50 mmole) in anhydrous acetone (600 ml) at 20°. The solid soon dissolved and after the mixture had been stirred at 20° for 1 hour it was chilled for 1 hour and the resulting solid was filtered off and washed with ether to give the title compound (33.1 g, 93%), m.p. 183° to 184°; [α]D21 + 24° (c 0.95 in DMSO); λinf.EtOH 235 nm (ε 14,500) and λinf.EtOH 256 nm (ε 8,820).

Workup

  1. dissolutionThe solid soon dissolved
  2. temperaturewas chilled for 1 hour
  3. filtrationthe resulting solid was filtered off
  4. washwashed with ether

Sources & evidence

ORD record
ord-3a8d77a0caf0402db9ce281547acb3f1
Source dataset
uspto-grants-1979_02
Patent number
US04138555

Reaction notes

Loading…