N-[(2-Fluorophenyl)sulfonyl]-D-phenylalanine → (2S)-2-(2-Fluorobenzenesulfonamido)-3-phenylpropanoic acid

HRID 1479921Notes

Reaction equation

HRID 1479921 reaction equation
[F:1][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].C(OC(=O)[C@H](CC1C=CC=CC=1)N)(C)(C)C>>[F:1][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:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:13]([OH:15])=[O:14])(=[O:9])=[O:10]

Participants

3

Reactant 2

HCID 2062364N-[(2-Fluorophenyl)sulfonyl]-D-phenylalanineHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoate

Product 1

HCID 697749(2S)-2-(2-Fluorobenzenesulfonamido)-3-phenylpropanoic acid

Procedure

Following the 14a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 14b as a colorless oil; (102.01 mg, 63.1%). [α]D25: +16.3 (c=0.39, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 7.82 (dd, J=1.8, 7.8 Hz, 1H), 7.59-7.52 (m, 1H), 7.26-7.21 (m, 4H), 7.15-7.08 (m, 3H), 5.27 (d, J=9 Hz, 1H), 4.43 (m, 1H), 3.20-3.05 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.53, 160.51, 157.15, 136.55, 134.91, 134.79, 129.48, 129.31, 128.18, 126.68, 124.15, 117.04, 116.75, 57.32, 38.37; HRMS (ESI): calcd for C15H14FNO4S: [M+Na]+=346.0508, obsd [M+Na]+=324.0520.

Sources & evidence

ORD record
ord-705a51baee7745cf98c5ec534d04ea37
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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