Water → HCID 19965984, compound

HRID 977848Notes

Reaction equation

HRID 977848 reaction equation
ClC(Cl)(Cl)[C:3]([N:5]=C=O)=[O:4].[C:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH:22]([OH:30])[CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:16][C:15]=1[NH:31][C:32](=[O:48])[CH2:33][CH:34]1[C:47]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:41][C:40]2[C:35]1=[CH:36][CH:37]=[CH:38][CH:39]=2)([CH3:13])([CH3:12])[CH3:11].C(=O)([O-])[O-].[Ca+2].O>C1C=CC=CC=1>[C:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH:22]([O:30][C:3](=[O:4])[NH2:5])[CH2:23][CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)=[CH:16][C:15]=1[NH:31][C:32](=[O:48])[CH2:33][CH:34]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=2[O:41][C:42]2[C:47]1=[CH:46][CH:45]=[CH:44][CH:43]=2)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 10112Calcium CarbonateHCID 76400Trichloroacetyl isocyanateHCID 19966195HCID 19966195, compound

Product 1

HCID 19965984HCID 19965984, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

64 μl (0.54 mmol) of trichloroacetyl isocyanate, were added to a solution of 272 mg (0.52 mmol) of N-[2-t-butyl-5-(4-cyclohexyl-3-hydroxybutyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Example 12) in 6 ml of benzene, and the resulting mixture was stirred for 10 minutes. At the end of this time, a methanolic solution of calcium carbonate was then added, whilst stirring. The reaction mixture was then mixed with water, and the organic phase was separated and dried. The solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 50 g of silica gel, using a 15:85 by volume mixture of ethyl acetate and methylene chloride as the eluent, to give 135 mg (yield 46%) of the title compound as a foam-like material.

Workup

  1. stirringwhilst stirring
  2. customthe organic phase was separated
  3. customdried
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customThe resulting residue was purified by column chromatography through 50 g of silica gel
  6. additionby volume mixture of ethyl acetate and methylene chloride as the eluent

Sources & evidence

ORD record
ord-aea90e81d1aa47a6a60342737799889e
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

Loading…