Sodium borohydride → HCID 59563789, compound

HRID 1020125Notes

Reaction equation

HRID 1020125 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:39])[CH:13]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31](=[O:38])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:25][CH:24]=3)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[BH4-].[Na+]>CCO>[OH:38][CH:31]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([CH:13]([C:12]([NH:11][C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[CH:1]=[N:2][CH:3]=[CH:4]3)=[O:39])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59563707HCID 59563707, compound

Product 1

HCID 59563789HCID 59563789, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To tert-butyl 3-(isoquinolin-6-ylamino)-3-oxo-2-(4-(2-oxo-2-phenylethoxy)phenyl)propylcarbamate (E275) in EtOH was added NaBH4 and the solution was stirred for 20 min at room temperature. The mixture was then poured into NaHCO3(sat) and extracted with CH2Cl2. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 5% MeOH/CH2Cl2) gave pure tert-butyl 2-(4-(2-hydroxy-2-phenylethoxy)phenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E276).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-14b4dc6a279a45daab80875731003e88
Source dataset
uspto-grants-2014_05
Patent number
US08716310B2

Reaction notes

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