Ammonium Chloride → HCID 58757355, compound

HRID 916692Notes

Reaction equation

HRID 916692 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]([C:16]([NH:19][S:20]([CH2:23][C:24]([F:27])([F:26])[F:25])(=[O:22])=[O:21])([CH3:18])[CH3:17])[CH:13]=[CH:14][CH:15]=2)[N:7]([CH3:28])[N:6]=1)=[O:4].[NH4+].[Cl-]>CCO>[OH:4][CH2:3][C:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[C:12]([C:16]([NH:19][S:20]([CH2:23][C:24]([F:27])([F:26])[F:25])(=[O:22])=[O:21])([CH3:18])[CH3:17])[CH:13]=[CH:14][CH:15]=2)[N:7]([CH3:28])[N:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 58757363HCID 58757363, compound

Product 1

HCID 58757355HCID 58757355, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (8.2 mg, 0.22 mmol) was added to a stirred solution of the aldehyde from Step 4 (85 mg, 0.22 mmol) in EtOH (5 mL) at RT and the mixture was stirred for a further 30 min. NH4Cl solution (5 ml) was added and the EtOH removed under reduced pressure. The aqueous residue was extracted with EtOAc (2×30 mL), and the organics dried and concentrated under reduced pressure to yield the crude alcohol (75 mg, 88%). 1H NMR (CDCl3, 360 MHz) δ 7.55-7.48 (2H, s), 7.42 (1H, t, J=7.5 Hz), 7.29 (1H, d, J=7.5 Hz), 6.25 (1H, s), 5.00 (1H, s), 4.64 (2H, s), 3.78 (3H, s), 3.41 (2H, q, J=8.9 Hz), 1.75 (6H, s). MS (ES+) C16H20F3N3O3S requires: 391, found: 392 (M+H+, 100%).

Workup

  1. customthe EtOH removed under reduced pressure
  2. extractionThe aqueous residue was extracted with EtOAc (2×30 mL)
  3. customthe organics dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9cc26c1a32bb48fc931e8c7b838ec4aa
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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