Water → HCID 58658571, compound

HRID 720954Notes

Reaction equation

HRID 720954 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][C:7]([NH:9][CH:10]1[C:20]2[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:19]=2[C:18]2[C:13](=[CH:14][C:15]([O:30][CH3:31])=[C:16]([O:28][CH3:29])[C:17]=2[O:26][CH3:27])[CH2:12][CH2:11]1)=[O:8].O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[S:2]([OH:5])([O:25][C:22]1[CH:23]=[CH:24][C:19]2[C:18]3[C:17]([O:26][CH3:27])=[C:16]([O:28][CH3:29])[C:15]([O:30][CH3:31])=[CH:14][C:13]=3[CH2:12][CH2:11][C@H:10]([NH:9][C:7](=[O:8])[CH3:6])[C:20]=2[CH:21]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 97865N-AcetylcolchicinolHCID 516892Sodium Bicarbonate

Product 1

HCID 58658571HCID 58658571, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

Chlorosulphonic acid (1 ml) was added at 0° C. in portions to a solution of pyridine (10 ml). After 15 minutes at 0° C., a solution of N-acetyl-colchicinol (1 g, 2.8 mmol) in pyridine (10 ml) was added. The solution was stirred overnight at ambient temperature. Water (30 ml) was added and the mixture was adjusted to pH8 by addition of sodium hydrogen carbonate. The aqueous layer was extracted with ether (3×20 ml) and purified on HP20SS resin, eluted with a 0–40% gradient of methanol/water. The volatiles were removed by evaporation to give (5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl hydrogen sulphate as a white solid.

Workup

  1. extractionThe aqueous layer was extracted with ether (3×20 ml)
  2. custompurified on HP20SS resin
  3. washeluted with a 0–40% gradient of methanol/water
  4. customThe volatiles were removed by evaporation

Sources & evidence

ORD record
ord-e0c7783676874c1998ce49d6d148739e
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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