Sodium borohydride → HCID 59625452, compound

HRID 2192863Notes

Reaction equation

HRID 2192863 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[C:6]([O:10][C:11]([NH:13][CH2:14][C@@H:15]([C:40](OC)=[O:41])[N:16]([C:21]([C:23]1[C:24]([NH:33][CH2:34][C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)=[N:25][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[N:27][CH:28]=1)=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:12])([CH3:9])([CH3:8])[CH3:7]>C(O)C.C1COCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:29]([C:26]1[N:25]=[C:24]([NH:33][CH2:34][C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)[C:23]([C:21]([N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C@H:15]([CH2:40][OH:41])[CH2:14][NH:13][C:11](=[O:12])[O:10][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:22])=[CH:28][N:27]=1)([CH3:30])([CH3:31])[CH3:32]

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 59625589HCID 59625589, compound

Product 1

HCID 59625452HCID 59625452, compoundYield 65.3%

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Calcium chloride (420 mg) was suspended in ethanol (5 ml), and sodium borohydride (286 mg) was added at 0° C. The mixture was stirred at 0° C. for 15 min, and a solution of methyl 3-[(tert-butoxycarbonyl)amino]-N-({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)-N-(2-methylpropyl)-L-alaninate (105 mg) in THF (5 ml) was added dropwise. The mixture was stirred at room temperature for 1.5 hr, the reaction mixture was diluted with 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to reversed-phase preparative HPLC, and fractions eluted with water-acetonitrile (9:1) to acetonitrile were collected. The mixture was basified (pH 10) with saturated aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the object compound (65 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 1.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washeluted with water-acetonitrile (9:1) to acetonitrile
  7. customwere collected
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialThe extract was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c5aad7010354805a4a25b1551f296de
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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