Dicyclohexylcarbodiimide → HCID 54402895, compound

HRID 1660328Notes

Reaction equation

HRID 1660328 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.[C:48]([O:52][C:53]([NH:55][CH2:56][CH2:57][N:58]1[C:63](=[O:64])[C:62](=[O:65])[NH:61][NH:60][C:59]1=[S:66])=[O:54])([CH3:51])([CH3:50])[CH3:49]>C(OCC)(=O)C>[C:48]([O:52][C:53]([NH:55][CH2:56][CH2:57][N:58]1[C:63](=[O:64])[C:62](=[O:65])[NH:61][N:60]=[C:59]1[S:66][C:20](=[O:22])[C:19](=[N:18][O:17][CH3:16])[C:23]1[N:24]=[C:25]([NH:28][C:29]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[S:26][CH:27]=1)=[O:54])([CH3:51])([CH3:49])[CH3:50]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acidHCID 15575766HCID 15575766, compound

Product 1

HCID 54402895HCID 54402895, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

N,N'-Dicyclohexylcarbodiimide (1.11 g) is added to a suspension, cooled to +4° C., of 2-methoxyimino-2-(2-tritylamino-thiazol-4-yl)-acetic acid, syn isomer (2.17 g) and 4-(2-tert.-butyoxycarbonylamino-ethyl)-5,6-dioxo-3-thioxo-perhydro-1,2,4-triazine (1.05 g) in ethyl acetate (50 cc). The mixture is stirred for 4 hours at 20° C., filtered and concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). The residue is taken up in methylene chloride (20 cc) and the solution is poured into diisopropyl ether (250 cc). After filtration and drying, 4-(2-tert.-butoxycarbonylamino-ethyl)-5,6-dioxo-3-[2-methoxyimino-2-(2-tritylamino-thiazol-4-yl)-acetylthio]-1,4,5,6-tetrahydro-1,2,4-triazine (syn isomer) (0.73 g) is obtained in the form of a yellow powder.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)
  3. additionthe solution is poured into diisopropyl ether (250 cc)
  4. filtrationAfter filtration
  5. customdrying

Sources & evidence

ORD record
ord-039e11bd1d714b868ebabe227f441cb0
Source dataset
uspto-grants-1981_12
Patent number
US04307116

Reaction notes

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