2-(r)-Cyclohexylmethyl-n-[1-(s)-methyl-2-(4-trifluoromethoxy-phenylamino)-ethyl]-4-oxo-4-thiomorpholin-4-yl-butyramide → 2-(r)-Cyclohexylmethyl-4-(1,1-dioxo-thiomorpholin-4-yl)-n-[1-(s)-methyl-2-(4-trifluoromethoxy-phenylamino)-ethyl]-4-oxo-butyramide

HRID 1783872Notes

Reaction equation

HRID 1783872 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH:7]1([CH2:13][C@H:14]([CH2:33][C:34](=[O:41])[N:35]2[CH2:40][CH2:39]S[CH2:37][CH2:36]2)[C:15]([NH:17][C@@H:18]([CH3:32])[CH2:19][NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>>[CH:7]1([CH2:13][C@H:14]([CH2:33][C:34]([N:35]2[CH2:40][CH2:39][S:3](=[O:5])(=[O:2])[CH2:37][CH2:36]2)=[O:41])[C:15]([NH:17][C@@H:18]([CH3:32])[CH2:19][NH:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:29])[F:30])=[CH:23][CH:22]=2)=[O:16])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 113068762-(r)-Cyclohexylmethyl-n-[1-(s)-methyl-2-(4-trifluoromethoxy-phenylamino)-ethyl]-4-oxo-4-thiomorpholin-4-yl-butyramideHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 112149482-(r)-Cyclohexylmethyl-4-(1,1-dioxo-thiomorpholin-4-yl)-n-[1-(s)-methyl-2-(4-trifluoromethoxy-phenylamino)-ethyl]-4-oxo-butyramide

Procedure

The compound was synthesized in a similar fashion to Example 6. An OXONE oxidation was employed title compound of Example 51 to furnish the sulfone. A procedure was used as described in McCarthy, J. R. et al. Org. Synth., CV9, 446. 1H NMR (CD3OD, 400 MHz) δ 0.73-0.79 (m, 2H), 1.00-1.19 (m, 7H), 1.10 (d, J=6.8 Hz), 1.34-1.75 (m, 6H), 2.34-2.37 (m, 1H), 2.64-2.71 (m, 2H), 2.94-3.08 (m, 7H), 3.79-4.01 (m, 5H), 6.53-6.56 (m, 2H), 6.87-6.89 (m, 2H). HPLC-MS calcd. for C25H36F3N3O5S (M+H+) 548.2, found 548.2.

Workup

  1. customThe compound was synthesized in a similar fashion to Example 6

Sources & evidence

ORD record
ord-7382ee2eb4ff48368b5a9b8708fcd1a2
Source dataset
uspto-grants-2009_03
Patent number
US07501408B2

Reaction notes

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