Hydrochloric Acid → HCID 360414, compound

HRID 1682248Notes

Reaction equation

HRID 1682248 reaction equation
[CH3:1][C:2]([NH:4][C@@H:5]1[C:21]2[C:14](=[CH:15][CH:16]=[C:17]([S:22][CH3:23])[C:18]([CH:20]=2)=[O:19])[C:13]2[C:8](=[CH:9][C:10]([OH:28])=[C:11]([O:26][CH3:27])[C:12]=2[O:24][CH3:25])[CH2:7][CH2:6]1)=[O:3].[CH2:29]([O:33][C:34](Cl)=[O:35])[CH2:30][CH2:31][CH3:32].Cl>N1C=CC=CC=1>[CH3:32][CH2:31][CH2:30][CH2:29][O:33][C:34]([O:28][C:10]1[CH:9]=[C:8]2[CH2:7][CH2:6][CH:5]([NH:4][C:2]([CH3:1])=[O:3])[C:21]3[C:14]([C:13]2=[C:12]([O:24][CH3:25])[C:11]=1[O:26][CH3:27])=[CH:15][CH:16]=[C:17]([S:22][CH3:23])[C:18](=[O:19])[CH:20]=3)=[O:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61140Butyl chloroformateHCID 840763-Demethylthiocolchicine

Product 1

HCID 360414HCID 360414, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-demethylthiocolchicine (100 mg) in pyridine (3 ml) is added with butylchloroformate (0.2 ml) under ice cooling. After 1 hour standing, the reaction mixture is adjusted to pH 5 by addition of 2N HCl and extracted with chloroform. After washing and drying as described in Example 5, 108 mg of 3-butoxycarbonyl-3demethylthiocolchicine is obtained as a yellow powder. mp 212°-215° C.; [α]D =-110.8° (c=0.3, CHCl3).

Workup

  1. extractionextracted with chloroform
  2. washAfter washing
  3. customdrying

Sources & evidence

ORD record
ord-30588cba08f04131a7051efe830ca922
Source dataset
uspto-grants-1992_12
Patent number
US05175342

Reaction notes

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