6-Fluoro-1-benzothiophene-2-carboxylic acid → (R)-2-(6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

HRID 1479918Notes

Reaction equation

HRID 1479918 reaction equation
Cl[C:2]1[C:3]2[CH:24]=[CH:23][C:22](C)=[CH:21][C:4]=2[S:5][C:6]=1[C:7]([NH:9][C@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])=[O:8].[F:26]C1C=CC2C=C(C(O)=O)SC=2C=1>>[F:26][C:22]1[CH:23]=[CH:24][C:3]2[CH:2]=[C:6]([C:7]([NH:9][C@H:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]([OH:13])=[O:12])=[O:8])[S:5][C:4]=2[CH:21]=1

Participants

3

Reactant 2

HCID 49624396-Fluoro-1-benzothiophene-2-carboxylic acidHCID 70598307HCID 70598307, compound

Product 1

HCID 59054584(R)-2-(6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acidYield 93.1%

Procedure

Following the 2a synthetic method, using 8-1-acid (98.10 mg, 0.5 mmol) instead of 3-chloro-6-methylbenzo[b]thiophene-2-carboxylic acid gave 13a as a colorless oil (159.84 mg, 93.1%). [α]D25: −21.1 (c=0.33, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.03 (d, J=8.1 Hz, 1H), 7.98 (s, 1H), 7.90-7.86 (m, 1H), 7.75-7.71 (m, 1H), 7.34-7.13 (m, 6H), 4.95-4.87 (m, 1H), 3.36-3.10 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 172.09, 163.11, 161.49, 159.87, 142.28, 139.46, 137.49, 136.19, 129.22, 128.33, 126.89, 126.63, 126.61, 124.44, 114.09, 108.67, 54.08, 37.01; HRMS (ESI): calcd for: C18H14FNO3S [M−H]−=342.0606, obsd [M−H]−=342.0594.

Sources & evidence

ORD record
ord-40a10de95d2345518e7e73539876f4d0
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

Loading…