Methyl Isocyanate → HCID 131711771, compound

HRID 1395693Notes

Reaction equation

HRID 1395693 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+].[CH3:45][N:46]=[C:47]=[O:48].C([O-])(O)=O.[Na+]>CN(C)C=O>[CH3:45][NH:46][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]

Participants

5

Reactant 3

HCID 12228Methyl Isocyanate3×HCID 516892Sodium BicarbonateHCID 131711769HCID 131711769, compound

Product 1

HCID 131711771HCID 131711771, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of the raw product of Step A of Example 1 was added under nitrogen to a mixture of 5 ml of dimethylformamide and 0.5 ml of methyl isocyanate at 5° C. and 0.5 ml of methyl isocyanate was added thereto. After 30 minutes at 5° C., another 0.5 ml of methyl isocyanate was added and after stirring 2 hours at room temperature, the mixture was poured into 75 ml of an aqueous 6% NaHCO3 solution. The mixture was extracted with ethyl acetate and the extracts were washed with sodium bicarbonate solution. The combined aqueous phases were added to ethyl acetate and the mixture was acidified with 6 N hydrochloric acid to a pH of 2. The mixture was decanted and the aqueous phase was extracted with ethyl acetate. The organic extracts were washed with water, dried and concentrated to dryness and the residue was empasted with isopropyl ether and was vacuum filtered. The product was taken up with methylene chloride and the solution was treated with activated carbon and was vacuum filtered. The filtrate was evaporated to dryness and the residue was crystallized from isopropyl ether to obtain 331 mg of 3-methylcarbamoyloxymethyl-7β-[2-(2-tritylamino-4-thiazolyl)-acetamido]-ceph-3-eme-4-carboxylic acid melting at about 210° C. Thin layer chromatography: Rf=0.42 (80-15-5-ethyl acetate-acetic acid-water).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extracts were washed with sodium bicarbonate solution
  3. additionThe combined aqueous phases were added to ethyl acetate
  4. customThe mixture was decanted
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. washThe organic extracts were washed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. filtrationfiltered
  10. additionthe solution was treated with activated carbon
  11. filtrationfiltered
  12. customThe filtrate was evaporated to dryness
  13. customthe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-2272e0d9fe5a4b3dabd0848afe94a10a
Source dataset
uspto-grants-1980_05
Patent number
US04205072

Reaction notes

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