Ammonium Chloride → HCID 86708061, compound

HRID 1524359Notes

Reaction equation

HRID 1524359 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:11][CH2:12][C:13]([F:17])([F:16])[CH:14]=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].[NH4+].[Cl-]>ClCCl.C(O)C>[Si:1]([O:8][CH2:9][C@@H:10]([N:18]([CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[S:19]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])=[CH:24][CH:23]=1)(=[O:20])=[O:21])[CH2:11][CH2:12][C:13]([F:16])([F:17])[CH2:14][OH:15])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86708062HCID 86708062, compound

Product 1

HCID 86708061HCID 86708061, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the material from Step 6 (1.17 g, 1.833 mmol) in dichloromethane (22 mL) and ethanol (14 mL) was added sodium borohydride (347 mg, 9.17 mmol). The reaction mixture was stirred at room temperature for 2 hours, poured into saturated aqueous NH4Cl and extracted with dichloromethane (2×). The combined organics were washed with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using EtOAc-hexanes to afford 625 mg of the title compound. LCMS (M+Na)=660.

Workup

  1. extractionextracted with dichloromethane (2×)
  2. washThe combined organics were washed with saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-eb5d9b2fafb24a9cb9c2e0270a8231f3
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

Loading…