4-Fluorobenzenesulfonyl chloride → (R)-2-(4-fluoro-benzenesulfonylamino)-3-phenyl-propionic acid

HRID 1479923Notes

Reaction equation

HRID 1479923 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:10])=[O:9].[F:23]C1C=CC(S(Cl)(=O)=O)=CC=1>>[F:23][C:6]1[CH:5]=[CH:4][C:3]([S:8]([NH:11][C@H:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([OH:15])=[O:14])(=[O:10])=[O:9])=[CH:2][CH:7]=1

Participants

3

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 2062364N-[(2-Fluorophenyl)sulfonyl]-D-phenylalanine

Product 1

HCID 737254(R)-2-(4-fluoro-benzenesulfonylamino)-3-phenyl-propionic acid

Procedure

Following the 14a synthetic method, using 4-fluorobenzenesulfonyl chloride (97.31 mg, 0.5 mmol) instead of 2-fluorobenzenesulfonyl chloride gave 16a as a colorless oil; (108.48 mg, 67.1%). [α]D25: −19.1 (c=0.41, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 7.77-7.73 (m, 2H), 7.24-7.21 (m, 7H), 6.92 (d, J=9 Hz, 1H), 4.21-4.14 (m, 1H), 3.15-2.90 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.55, 166.28, 162.95, 137.53, 136.53, 129.74, 129.62, 129.39, 128.24, 126.68, 115.93, 115.63, 57.29, 38.49; HRMS (ESI): calcd for: C15H14FNO4S [M+Na]+=346.0520, obsd [M+Na]+=346.0513.

Sources & evidence

ORD record
ord-58f2c1b83c364587b133dad11d8cab9e
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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