Methional → HCID 69748555, compound

HRID 1062389Notes

Reaction equation

HRID 1062389 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][S:16][CH2:17][CH2:18][CH:19]=O.[Cl:21][C:22]1[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:23]=1[NH:29][C:30](=[O:38])[C@:31]([OH:37])([CH3:36])[C:32]([F:35])([F:34])[F:33].C(=O)([O-])O.[Na+]>ClCCCl>[Cl:21][C:22]1[CH:27]=[C:26]([NH:28][CH2:19][CH2:18][CH2:17][S:16][CH3:15])[CH:25]=[CH:24][C:23]=1[NH:29][C:30](=[O:38])[C@:31]([OH:37])([CH3:36])[C:32]([F:34])([F:33])[F:35]

Participants

6

Reactant 4

HCID 18635MethionalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 54520116HCID 54520116, compound

Product 1

HCID 69748555HCID 69748555, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.297 g) was added to a solution of 3-methylsulphanylpropionaldehyde (0.1 ml) and (R)-N-(2-chloro-4-aminophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 208) (0.282 g) in 1,2-dichloroethane (6 ml). The mixture was stirred for 16 hours. Saturated aqueous sodium hydrogen carbonate (25 ml) was added and the mixture was extracted with ethyl acetate (40 ml). The extracts were washed with brine (15 ml) then dried. Volatile material was removed by evaporation and the residue was purified by chromatography on a Varian Isolute silica column eluting with 25% ethyl acetate/hexane. The resulting solid was triturated with ether to give the title compound (0.089 g) as a solid. NMR: 1.54 (s, 3H), 1.78 (m, 2H), 2.05 (s, 3H), 2.55 (q, 2H), 3.09 (q, 2H), 5.93 (t, 1H), 6.54 (dd, 1H), 6.65 (s, 1H), 7.46 (m, 2H), 9.33 (s, 1H); MS (ESP−): 369.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (40 ml)
  2. washThe extracts were washed with brine (15 ml)
  3. customthen dried
  4. customVolatile material was removed by evaporation
  5. customthe residue was purified by chromatography on a Varian Isolute silica column
  6. washeluting with 25% ethyl acetate/hexane
  7. customThe resulting solid was triturated with ether

Sources & evidence

ORD record
ord-0199bc1e4d4e459fb662b163d8d82348
Source dataset
uspto-grants-2005_11
Patent number
US06960688B2

Reaction notes

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