Hydrochloric Acid → N-(2-t-Butyl-5-{3-[2-(1-imidazolyl)acetoxy]-4-cyclohexylbutyl}phenyl)-2-(9H-xanthen-9-yl)acetamide hydrochloride

HRID 1734887Notes

Reaction equation

HRID 1734887 reaction equation
O1CCOCC1.[ClH:7].[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH:20]([O:28][C:29](=[O:36])[CH2:30][N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:14][C:13]=1[NH:37][C:38](=[O:54])[CH2:39][CH:40]1[C:53]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[O:47][C:46]2[C:41]1=[CH:42][CH:43]=[CH:44][CH:45]=2)([CH3:11])([CH3:10])[CH3:9]>C(OCC)C>[ClH:7].[C:8]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH:20]([O:28][C:29](=[O:36])[CH2:30][N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:14][C:13]=1[NH:37][C:38](=[O:54])[CH2:39][CH:40]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:46]=2[O:47][C:48]2[C:53]1=[CH:52][CH:51]=[CH:50][CH:49]=2)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 19966206HCID 19966206, compound

Product 1

HCID 19966205N-(2-t-Butyl-5-{3-[2-(1-imidazolyl)acetoxy]-4-cyclohexylbutyl}phenyl)-2-(9H-xanthen-9-yl)acetamide hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

200 μl of a 4N dioxane solution of hydrogen chloride were added to a solution of 339 mg (0.54 mmol) of N-(2-t-butyl-5-{3-[2-(1-imidazolyl)acetoxy]-4-cyclohexylbutyl}phenyl)-2-(9H-xanthen-9-yl)acetamide [prepared as described in step (i) above] in 3 ml of diethyl ether, and the crystals which precipitated were collected by filtration and washed with diethyl ether. The crystals were purified by high performance liquid chromatography through ODS (120 A, φ 30 mm×250 mm) using a 3:1 by volume mixture of acetonitrile and water as the eluent, to give a gel. This gel was crystallized by trituration with diethyl ether, to give 170 mg (yield 85%) of the title compound as colorless crystals, melting at 125°-133° C.

Workup

  1. customthe crystals which precipitated
  2. filtrationwere collected by filtration
  3. washwashed with diethyl ether
  4. customThe crystals were purified by high performance liquid chromatography through ODS (120 A, φ 30 mm×250 mm)
  5. additionby volume mixture of acetonitrile and water as the eluent
  6. customto give a gel
  7. customThis gel was crystallized by trituration with diethyl ether

Sources & evidence

ORD record
ord-4fc632f9ae7d4c94b6032826e7a67b79
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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