Hydrochloric Acid → HCID 19966249, compound

HRID 1734872Notes

Reaction equation

HRID 1734872 reaction equation
Cl.O1CCCC1.[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([O:26][Si](C(C)(C)C)(C)C)[CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:13][C:12]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:10])([CH3:9])[CH3:8].C(OCC)(=O)C>O>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH:18]([OH:26])[CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:13][C:12]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 19966119HCID 19966119, compound

Product 1

HCID 19966249HCID 19966249, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1.5 ml of 2N aqueous hydrochloric acid were added to 15 ml of a tetrahydrofuran solution containing 813 mg (1.30 mmol) of N-[2-t-butyl-5-(3-cyclohexyl-2-t-butyl-dimethylsilyloxypropyl)phenyl]-2-(9H-xanthen-9-yl)-acetamide (prepared by a procedure similar to that described in Preparation 11), and the mixture was stirred for 2.5 hours at 50° C. The reaction mixture was then allowed to return to room temperature. Addition of a mixture of ethyl acetate and water caused the title compound to be distributed between the organic solvent and water. The organic layer was separated and washed with a saturated aqueous solution of sodium hydrogen carbonate, and then with a saturated aqueous solution of sodium chloride. The solvent was removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 50 g of silica gel. Elution with mixtures of ethyl acetate and hexane ranging from 1:2 to 2:3 by volume afforded 650 mg (yield 98%) of the title compound as crystals, melting at 177°-178° C. (after recrystallization from diisopropyl ether).

Workup

  1. customprepared by a procedure similar to
  2. customthat described in Preparation 11), and the mixture
  3. customto return to room temperature

Sources & evidence

ORD record
ord-3cc473bba1b74f408fea20beceb55371
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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