3-Chloro-6-fluorobenzo[b]thiophene-2-carboxylic acid → N-[(3-Chloro-6-fluorobenzo[b]thien-2-yl)carbonyl]-D-phenylalanine
Reaction equation
[Cl:1][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].ClC1C2C=CC([F:39])=CC=2SC=1C(O)=O>>[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][C:22]([F:39])=[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]Participants
3
Procedure
Following the 2a synthetic method, using 3-chloro-6-fluorobenzo[b]thiophene-2-carboxylic acid (115.32 mg, 0.5 mmol) instead of 3-chloro-6-methylbenzo[b]thiophene-2-carboxylic acid gave 4a as a white powder; (177.01 mg, 93.7%). [α]D25: −21.9 (c=0.37, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.95-7.76 (m, 3H), 7.44-7.22 (m, 6H), 5.04-4.97 (m, 1H), 3.45-3.26 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.48, 163.90, 160.62, 159.50, 139.15, 136.67, 133.50, 129.50, 128.40, 126.89, 124.94, 118.57, 115.15, 114.82, 109.30, 108.95, 53.95, 36.78; HRMS (ESI): calcd for: C18H13ClFNO3S [M+H]+=378.0361, obsd [M+H]+=378.0347.
Sources & evidence
- ORD record
- ord-bc75fd639d794d1693243bddfcf53a7b
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409880B2
Reaction notes
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