Trichloroacetyl isocyanate → HCID 131711768, compound

HRID 1395692Notes

Reaction equation

HRID 1395692 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:42])[CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[S:20][CH:21]=3)[C:12](=[O:43])[N:7]2[C:8]=1[C:9]([O-:11])=[O:10].[Na+].ClC(Cl)(Cl)[C:47]([N:49]=C=O)=[O:48].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:47]([O:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:42])[CH2:16][C:17]3[N:18]=[C:19]([NH:22][C:23]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[S:20][CH:21]=3)[C:12](=[O:43])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10])(=[O:48])[NH2:49]

Participants

5

Reactant 3

HCID 76400Trichloroacetyl isocyanateHCID 516892Sodium BicarbonateHCID 131711769HCID 131711769, compound

Product 1

HCID 131711768HCID 131711768, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8 g of raw product of Step A were added with stirring at room temperature to a solution of 8 g of trichloroacetyl isocyanate in 160 ml of dry methylene chloride and after stirring for 15 minutes, 1.6 liters of a solution of aqueous 6% sodium bicarbonate were added thereto. The mixture was stirred at room temperature overnight and was then extracted with ethyl acetate. The organic phase was removed and the aqueous phase was acidified with 6 N hydrochloric acid to a pH of 2 in the presence of ethyl acetate. The organic phase was washed with water, dried and concentrated under reduced pressure to 30 ml. The product was precipitated by addition of isopropyl ether and the mixture was filtered and dried to obtain 2.7 g of 3-carbamoyloxymethyl-7β-[2-(2-tritylamino-4-thiazolyl)-acetamido]-ceph-3-eme-4-carboxylic acid melting at about 200° C. with decomposition.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionwas then extracted with ethyl acetate
  3. customThe organic phase was removed
  4. washThe organic phase was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure to 30 ml
  7. customThe product was precipitated by addition of isopropyl ether
  8. filtrationthe mixture was filtered
  9. customdried

Sources & evidence

ORD record
ord-dba2993f442b444a8a4fafd185557832
Source dataset
uspto-grants-1980_05
Patent number
US04205072

Reaction notes

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