N-[(2-Fluorophenyl)sulfonyl]-D-phenylalanine → (R)-2-(3-fluorophenylsulfonamido)-3-phenylpropanoic acid

HRID 1479922Notes

Reaction equation

HRID 1479922 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=C(S(Cl)(=O)=O)C=CC=1>>[F:23][C:7]1[CH:2]=[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:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 2062364N-[(2-Fluorophenyl)sulfonyl]-D-phenylalanineHCID 27342583-Fluorobenzenesulfonyl Chloride

Product 1

HCID 68173889(R)-2-(3-fluorophenylsulfonamido)-3-phenylpropanoic acid

Procedure

Following the 14a synthetic method, using 3-fluorobenzenesulfonyl chloride (66.19 μL, 0.5 mmol) instead of 2-fluorobenzenesulfonyl chloride gave 15a as a colorless oil; (103.95 mg, 64.3%). [α]D25: −16.5 (c=0.31, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 7.49-7.32 (m, 3H), 7.25-7.20 (m, 4H), 7.10-7.08 (m, 2H), 5.45 (d, J=7.8 Hz, 1H), 4.25 (m, 1H), 3.19-2.91 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 163.89, 160.56, 141.51, 134.71, 130.88, 129.34, 128.68, 127.47, 122.75, 120.24, 119.96, 114.49, 114.17, 56.86 38.74; HRMS (ESI): calcd for: C15H14FNO4S [M−H]−=322.0555, obsd [M−H]−=322.0549.

Sources & evidence

ORD record
ord-e706515c40114b65a8651b83bd67eb6d
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

Loading…