Trichloroacetyl isocyanate → HCID 14556140, compound

HRID 745967Notes

Reaction equation

HRID 745967 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:22]([NH:23][C:24](=[O:31])[CH2:25][C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)[C:21](=[O:32])[N:16]2[C:17]=1[C:18]([OH:20])=[O:19]>C(OCC)(=O)C>[S:27]1[CH:28]=[CH:29][CH:30]=[C:26]1[CH2:25][C:24]([NH:23][C@@H:22]1[C:21](=[O:32])[N:16]2[C:17]([C:18]([OH:20])=[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:31]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 930153-(Hydroxymethyl)-7-{[1-hydroxy-2-(thiophen-2-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 14556140HCID 14556140, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Trichloroacetylisocyanate (4.3 ml) was added rapidly to a stirred suspension of (6R,7R)-3-hydroxymethyl-7-(2-thienylacetamido)ceph-3-em-4-carboxylic acid (10.62 g) at 6° in ethyl acetate (70 ml). The reaction mixture was stirred at 5° for 40 min. Petroleum ether was added dropwise during 15 min. The mixture was stirred for 30 min, filtered and the solid was washed with petroleum ether and dried to give the title compound as a solid (16.48 g), [α]D22 +73° (c 1.2 in Me2SO).

Workup

  1. stirringThe mixture was stirred for 30 min
  2. filtrationfiltered
  3. washthe solid was washed with petroleum ether
  4. customdried

Sources & evidence

ORD record
ord-b961cb4450504efd8ca8a78f04f61b05
Source dataset
uspto-grants-1986_07
Patent number
US04602012

Reaction notes

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