Sodium borohydride → HCID 69254543, compound

HRID 31366Notes

Reaction equation

HRID 31366 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[C:15]([Br:16])=[C:14]2[C:10]([CH:11]=[N:12][N:13]2[CH2:17][C@@H:18]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH3:19])=[CH:9][CH:8]=1)C.[BH4-].[Na+].[Cl-].[Ca+2].[Cl-]>O1CCCC1.C(O)C>[CH2:24]([O:23][C:21](=[O:22])[NH:20][C@@H:18]([CH3:19])[CH2:17][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([O:6][CH2:5][CH2:4][OH:3])[C:15]=2[Br:16])[CH:11]=[N:12]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydride2×HCID 5284359Calcium ChlorideHCID 69253335[1-((S)-2-Benzyloxycarbonylamino-propyl)-7-bromo-1H-indazol-6-yloxy]-acetic acid ethyl ester

Product 1

HCID 69254543HCID 69254543, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the acetate from Step B (0.90 g, 1.84 mmol) in a mixture of tetrahydrofuran (20 mL) and ethanol (20 mL) was added sodium borohydride (70 mg, 1.84 mmol) and calcium chloride (0.21 g, 1.84 mmol) with stirring. The suspension was stirred at ambient temperature for 1 h and more sodium borohydride (70 mg, 1.84 mmol) was added. The reaction was monitored by TLC until no starting material remained. The volatiles were evaporated and the residue mixed with water and extracted with ethyl acetate (3×50 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness. Chromatography on silica eluting with a gradient of 20% to 50% EtOAc/hexane gave a solid (0.67 g, 82%): mp 97-99° C.; LCMS (+APCI) 448, 450 (M+H).

Workup

  1. stirringThe suspension was stirred at ambient temperature for 1 h
  2. customThe volatiles were evaporated
  3. additionthe residue mixed with water
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-428869e50940453ba6db18694d112ca6
Source dataset
uspto-grants-2008_09
Patent number
US07425572B2

Reaction notes

Loading…