3-Bromo-1-propanol → HCID 69749686, compound

HRID 2301050Notes

Reaction equation

HRID 2301050 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([S:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:11])[CH:7]=[CH:6][C:5]=1[NH:19][C:20](=[O:28])[C@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23].Br[CH2:30][CH2:31][CH2:32][OH:33]>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([S:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:30][CH2:31][CH2:32][OH:33])=[CH:14][CH:13]=2)=[O:11])[CH:7]=[CH:6][C:5]=1[NH:19][C:20](=[O:28])[C@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:23])[F:24]

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 69751875HCID 69751875, compound

Product 1

HCID 69749686HCID 69749686, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.06 g of a 60% dispersion in oil) was added to a solution of (R)-N-[2-chloro-4-(4-hydroxyphenylsulphinyl)phenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 89) (0.5 g) in DMF (5 ml) at 0° C. The mixture was stirred for 15 minutes then 3-bromopropanol (0.12 ml) was added as a solution in DMF (3 ml). The mixture was stirred at ambient temperature for 16 hours. Volatile material was removed by evaporation and the residue was purified by chromatography on a silica gel Mega Bond Elut column eluting with 0-10% methanol/DCM to give the title compound (0.34 g) as a gum. NMR (CDCl3): 1.25 (dd, 2H), 1.7 (s, 3H), 1.8 (s, 1H), 3.8-3.9 m, 2H), 4.1-4.2 (m, 2H), 5.1 (s, 1H), 6.95 (d, 2H), 7.4 (d, 1H), 7.5 (d, 2H), 7.6-7.65 (m, 1H), 8 45-8.55 (m, 1H), 9.3 (s, 1H); MS (ESP−): 464.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 16 hours
  2. customVolatile material was removed by evaporation
  3. customthe residue was purified by chromatography on a silica gel Mega Bond Elut column
  4. washeluting with 0-10% methanol/DCM

Sources & evidence

ORD record
ord-adecdac010d6400eb38f2e238e3afc4f
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

Loading…