3,3,3-Trifluoropropane-1-sulfonyl chloride → (S)-methyl 2-(3,3,3-trifluoro-N-methylpropylsulfonamido)hex-5-enoate

HRID 501676Notes

Reaction equation

HRID 501676 reaction equation
Cl.[CH3:2][NH:3][C@@H:4]([CH2:9][CH2:10][CH:11]=[CH2:12])[C:5]([O:7][CH3:8])=[O:6].[F:13][C:14]([F:22])([F:21])[CH2:15][CH2:16][S:17](Cl)(=[O:19])=[O:18]>>[F:13][C:14]([F:22])([F:21])[CH2:15][CH2:16][S:17]([N:3]([C@@H:4]([CH2:9][CH2:10][CH:11]=[CH2:12])[C:5]([O:7][CH3:8])=[O:6])[CH3:2])(=[O:19])=[O:18]

Participants

3

Reactant 2

HCID 27611773,3,3-Trifluoropropane-1-sulfonyl chlorideHCID 86622315(S)-methyl 2-(methylamino)hex-5-enoate hydrochloride

Product 1

HCID 86622317(S)-methyl 2-(3,3,3-trifluoro-N-methylpropylsulfonamido)hex-5-enoateYield 56%

Procedure

Step M (1): Same procedure as Step I (1). (S)-Methyl 2-(methylamino)hex-5-enoate hydrochloride from Step K (2) was sulfonylated with 3,3,3-trifluoropropane-1-sulfonyl chloride according to the procedure outlined in Step I (1). The procedure provided 242 mg (56% yield) of (S)-methyl 2-(3,3,3-trifluoro-N-methylpropylsulfonamido)hex-5-enoate. LC-MS (M+H)+=318.3; 1H NMR (500 MHz, CDCl3) δ ppm 1.73-1.85 (m, 1H) 2.02-2.21 (m, 3H) 2.59-2.73 (m, 2H) 2.87 (s, 3H) 3.16-3.32 (m, 2H) 3.76 (s, 3H) 4.55 (dd, J=10.68, 4.58 Hz, 1H) 4.99-5.14 (m, 2H) 5.74-5.87 (m, 1H).

Sources & evidence

ORD record
ord-8822542aeb344229b2e6bf10fe05d598
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

Loading…