Acetic Acid → HCID 70979365, compound

HRID 2271340Notes

Reaction equation

HRID 2271340 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:26]=1)[O:19][CH2:20][C:21](=O)[CH3:22].[CH2:31]([NH2:34])[CH2:32][CH3:33].C(O)(=O)C>ClCCCl>[F:15][C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([S:27]([CH3:30])(=[O:29])=[O:28])[CH:26]=1)[O:19][CH2:20][CH:21]([NH:34][CH2:31][CH2:32][CH3:33])[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7852PropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 70979744HCID 70979744, compound

Product 1

HCID 70979365HCID 70979365, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (1.16 g, 5.51 mmol) was added to a stirred mixture of 1-(3-fluoro-5-methylsulfonyl-phenoxy)propan-2-one (0.905 g, 3.67 mmol), propylamine (0.24 g, 4.04 mmol), acetic acid (0.5 g, 8.33 mmol) and molecular sieves (2 g, 4 Å, 4-8 mesh) in dry 1,2-dichloroethane (20 ml) the mixture was stirred at ambient temperature for 24 h, the suspension was filtrated and sodium carbonate (100 ml, 10% aqueous solution) was added. The aqueous phase was extracted with dichloromethane (3×50 ml). The combined organic phase was dried with Na2SO4 and evaporated. Purification on flash chromatography (ethyl acetate:methanol 1:0 to 4:1). 0.3 g, 28%. MS m/z (relative intensity, 70 eV) 289 (M+, 1), 260 (9), 152 (4), 87 (6), 86 (bp).

Workup

  1. filtrationthe suspension was filtrated
  2. additionsodium carbonate (100 ml, 10% aqueous solution) was added
  3. extractionThe aqueous phase was extracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined organic phase was dried with Na2SO4
  5. customevaporated
  6. customPurification on flash chromatography (ethyl acetate:methanol 1:0 to 4:1)

Sources & evidence

ORD record
ord-10c84a673d2644449a9b975aeda12730
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

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