Sodium borohydride → Trityllosartan

HRID 1033602Notes

Reaction equation

HRID 1033602 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[N:20]=[N:21][N:22]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:23]=2)=[CH:9][CH:8]=1)(=O)=O.[CH2:43]([C:47]1[NH:48][C:49]([CH:53]=[O:54])=[C:50]([Cl:52])[N:51]=1)[CH2:44][CH2:45][CH3:46].[BH4-].[Na+]>O>[CH2:43]([C:47]1[N:48]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]3[N:20]=[N:21][N:22]([C:24]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:23]=3)=[CH:11][CH:12]=2)[C:49]([CH2:53][OH:54])=[C:50]([Cl:52])[N:51]=1)[CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 103708395-(4'-Methanesulfonyloxymethyl-1,1'-biphenyl-2-yl)-2-triphenylmethyl-2H-tetrazoleHCID 178418251HCID 178418251, compound

Product 1

HCID 10865273Trityllosartan

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To the reaction mixture of Example 10 was added 2-n-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (0.01 m=1.86 g). The reaction was stirred overnight at room temperature. Water (0.87 mL) was added dropwise followed by sodium borohydride pellets (0.37 g). After stirring for 5 hours, the reaction mixture was added slowly to 100 mL water containing 3 mL acetone. The temperature was maintained at about 25° C. during the addition. The resultant slurry was stirred for an additional 45 minutes, then filtered. The solid was rinsed with two 50 mL portions of water. The wet cake was recrystallized first from 50 mL of n-butyl chloride, then from 30 mL of ethyl acetate to give 1.95 g title compound in 28% overall yield; mp 168°-169° C.

Workup

  1. stirringAfter stirring for 5 hours
  2. temperatureThe temperature was maintained at about 25° C. during the addition
  3. stirringThe resultant slurry was stirred for an additional 45 minutes
  4. filtrationfiltered
  5. washThe solid was rinsed with two 50 mL portions of water
  6. customThe wet cake was recrystallized first from 50 mL of n-butyl chloride

Sources & evidence

ORD record
ord-610762dd4f344f8d80a5c1f1824d66ed
Source dataset
uspto-grants-1994_05
Patent number
US05310928

Reaction notes

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