D-Tartaric acid → HCID 13825850, compound

HRID 2352429Notes

Reaction equation

HRID 2352429 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:14]2([OH:24])[CH:21]3[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)[N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:5]=[CH:6][CH:7]=1.[C:25]([OH:34])(=[O:33])[C@H:26]([C@@H:28]([C:30]([OH:32])=[O:31])[OH:29])[OH:27]>CO.C(#N)C>[C:30]([CH:28]([CH:26]([C:25]([OH:34])=[O:33])[OH:27])[OH:29])([OH:32])=[O:31].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:14]2([OH:24])[CH:15]3[CH2:23][CH:19]4[CH2:18][CH:17]([CH2:22][CH:21]2[CH2:20]4)[CH2:16]3)[N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 439655D-Tartaric acidHCID 9862895HCID 9862895, compound

Product 1

HCID 13825850HCID 13825850, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

43.0 g (125.4 mmol) of (3-chlorophenyl)-(2-hydroxy-2-adamantyl)-(1-imidazolyl)-methane and 18.83 g (125.4 mmol) of D(-)-tartaric acid were dissolved in a mixture of 67 ml of methanol and 440 ml of acetonitrile at the boiling point. When the solution was slowly cooled to room temperature, crystallization occurred. After 2 days, the crystals were filtered off under suction and washed with acetonitrile and ether and dried for 3 hours at 98° C./3-6 mbar. 23.50 g of (3-chlorophenyl)-(2-hydroxy-2-adamantyl)-(1-imidazolyl)-methane hydrogen tartrate ([α]D : (+) 4.26° (c=1.0, CH3OH)) were obtained. This product was dissolved in a boiling mixture of 33 ml of methanol and 193 ml of acetonitrile and allowed to crystallize out at room temperature. After isolation as described above, 18.00 g of product [α]D22 : (+) 5.30° (c=1.0, CH3OH)) were obtained. These 18.00 g were recrystallized in an analogous manner from 26 ml of methanol and 151 ml of acetonitrile. 14.2 g of product [α]D22 : (+) 5.53° (c=1.0, CH3OH)) were obtained. A further recrystallization from 20 ml of methanol and 116 ml of acetonitrile gave 11.7 g of product ([α]D22 : (+) 5.90° (c=1.0, CH3OH)). Further recrystallization of this substance from 16 ml of methanol and 95 ml of acetonitrile in 9.60 g of (3-chlorophenyl)-(2-hydroxy-2-adamantyl)-(1-imidazolyl)-methane hydrogen tartrate ([α]D22 : (+) 6.18° (c=1.0, CH 3 OH)) as a pure diastereomeric salt of melting point 112°-113° C. (decomposition).

Workup

  1. customcrystallization
  2. filtrationthe crystals were filtered off under suction
  3. washwashed with acetonitrile and ether
  4. customdried for 3 hours at 98° C./3-6 mbar

Sources & evidence

ORD record
ord-8603e4dab0a34365b8bafba7ea58c09a
Source dataset
uspto-grants-1989_10
Patent number
US04876354

Reaction notes

Loading…