Dicyclohexylcarbodiimide → HCID 54066929, compound

HRID 851568Notes

Reaction equation

HRID 851568 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][O:17][N:18]=[C:19]([C:23]1[N:24]=[C:25]([NH:28][C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[S:26][CH:27]=1)[C:20]([OH:22])=O.[CH3:48][O:49][CH:50]([O:61][CH3:62])[CH2:51][N:52]1[C:57](=[O:58])[C:56](=[O:59])[NH:55][NH:54][C:53]1=[S:60]>CN(C)C=O>[CH3:62][O:61][CH:50]([O:49][CH3:48])[CH2:51][N:52]1[C:57](=[O:58])[C:56](=[O:59])[NH:55][N:54]=[C:53]1[S:60][C:20](=[O:22])[C:19](=[N:18][O:17][CH3:16])[C:23]1[N:24]=[C:25]([NH:28][C:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[S:26][CH:27]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 13175918HCID 13175918, compound

Product 1

HCID 54066929HCID 54066929, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
4 °C

Procedure

N,N'-Dicyclohexylcarbodiimide (0.50 g) is added all at once to a solution, cooled to 4° C., of the syn isomer of 2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (0.89 g) and 4-(2,2-dimethoxyethyl)-5,6-dioxo-3-thioxo-perhydro-1,2,4-triazine (0.47 g) in dimethylformamide (20 cc); the mixture is stirred for 1 hour at 4° C. and then for 3 hours at 20° C. The reaction suspension is filtered, the filtrate is diluted with ethyl acetate (100 cc), the mixture is washed with water (2×50 cc), a 1% strength solution of sodium bicarbonate (2×50 cc) and a semi-saturated solution of sodium chloride (2×50 cc), dried over sodium sulphate and filtered and the filtrate is concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). The residue is triturated in isopropyl ether (10 cc) and, after filtration and drying, the syn isomer of 4-(2,2-dimethoxyethyl)-5,6-dioxo-3-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)-acetylthio]-1,4,5,6-tetrahydro-1,2,4-triazine (0.91 g) is obtained in the form of a yellow powder.

Workup

  1. waitfor 3 hours at 20° C
  2. filtrationThe reaction suspension is filtered
  3. additionthe filtrate is diluted with ethyl acetate (100 cc)
  4. washthe mixture is washed with water (2×50 cc)
  5. dry with materiala 1% strength solution of sodium bicarbonate (2×50 cc) and a semi-saturated solution of sodium chloride (2×50 cc), dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)
  8. customThe residue is triturated in isopropyl ether (10 cc)
  9. filtrationafter filtration
  10. customdrying

Sources & evidence

ORD record
ord-493ab244fbfa4128bb704b4a8bff7a6c
Source dataset
uspto-grants-1983_05
Patent number
US04385181

Reaction notes

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