Ethanol → HCID 21879609, compound

HRID 420225Notes

Reaction equation

HRID 420225 reaction equation
C(O)C.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[CH:9]([N:12]([CH:57]([CH3:59])[CH3:58])[C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([C:25]([OH:56])([C:32]1[N:33]=[CH:34][N:35]([C:37]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:36]=1)[CH2:26][C:27](OCC)=[O:28])[CH:19]=[CH:18]2)=[O:14])([CH3:11])[CH3:10]>O.C1COCC1>[OH:56][C:25]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:13]([N:12]([CH:57]([CH3:59])[CH3:58])[CH:9]([CH3:10])[CH3:11])=[O:14])[CH:24]=[CH:23]2)([C:32]1[N:33]=[CH:34][N:35]([C:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=1)[CH2:26][CH2:27][OH:28]

Participants

7

Reactant 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 17968408HCID 17968408, compound

Product 1

HCID 21879609HCID 21879609, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 mL of ethanol and 1.5 mL of THF were added to 0.11 g (2.94 mmol, 8 eq) of sodium borohydride. 0.16 g (1.47 mmol, 4 eq) of calcium chloride was added at 0° C., and the mixture was stirred at 0˜3° C. for 25 minutes. 0.25 g (0.37 mmol) of ethyl 3-{6-[(diisopropylamino)carbonyl]-2-naphthyl}-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)propanoate was added at 0° C. The mixture was stirred at 20˜23° C. for 8 hours and 15 minutes. 13 mL of water was added dropwise, and the mixture was stirred at 25° C. for 15 minutes. Crystals were filtered, and washed with water. Vacuum drying (50° C.) to a constant weight afforded 0.21 g of 6-[1,3-dihydroxy-1-(1-trityl-1H-imidazol-4-yl)propyl]-N,N-diisopropyl-2-naphthamide (yield 90%).

Workup

  1. stirringThe mixture was stirred at 20˜23° C. for 8 hours and 15 minutes
  2. stirringthe mixture was stirred at 25° C. for 15 minutes
  3. filtrationCrystals were filtered
  4. washwashed with water
  5. customVacuum drying (50° C.) to a constant weight

Sources & evidence

ORD record
ord-b007a0a3350b408ba1366b38fbdad566
Source dataset
uspto-grants-2012_01
Patent number
US08093403B2

Reaction notes

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