Sodium borohydride → HCID 58823230, compound

HRID 459418Notes

Reaction equation

HRID 459418 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:31][CH2:32][C:33](=[O:59])[CH2:34][C:35]([O:37][C@H:38]([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:39]([OH:52])([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:36])[C:10]([CH:28]([CH3:30])[CH3:29])=[C:11]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:31][CH2:32][C@@H:33]([OH:59])[CH2:34][C:35]([O:37][C@H:38]([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[C:39]([OH:52])([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[O:36])[C:10]([CH:28]([CH3:30])[CH3:29])=[C:11]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58823231HCID 58823231, compound

Product 1

HCID 58823230HCID 58823230, compoundYield 940.6%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 5-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]-3-oxo-1-pentanoic acid, (R)-2-hydroxy-1,2,2-triphenylethyl ester (0.1 g, 0.127 mmol., 7) in 6 ml of THF/MeOH (1:2, v/v) was cooled to −78° C. To this solution was added sodium borohydride (20 mg) in two portions over a period of 0.5 h. The resulting reaction mixture was stirred at −78° C. for an additional 1 hour under nitrogen and then quenched with aqueous saturated NH4Cl solution and extracted with dichloromethane (10 mL×2). The combined dichloromethane layers were washed with brine (5 mL×2), dried (Na2SO4) and evaporated to give a white crystalline solid (0.94 g, 94%).

Workup

  1. customThe resulting reaction mixture
  2. customquenched with aqueous saturated NH4Cl solution
  3. extractionextracted with dichloromethane (10 mL×2)
  4. washThe combined dichloromethane layers were washed with brine (5 mL×2)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-df3cd5c899b948729c748bd8ba5304ca
Source dataset
uspto-grants-2007_03
Patent number
US07193090B2

Reaction notes

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