3-Chloro-5-fluorobenzo[b]thiophene-2-carbonyl chloride → (R)-2-(3-chloro-5-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

HRID 1479916Notes

Reaction equation

HRID 1479916 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=C[C:22]([C:25](F)([F:27])F)=[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=C(F)C=CC=2SC=1C(Cl)=O>>[Cl:1][C:2]1[C:3]2[CH:24]=[C:25]([F:27])[CH:22]=[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

Reactant 2

HCID 148724863-Chloro-5-fluorobenzo[b]thiophene-2-carbonyl chlorideHCID 70558597(R)-2-(3-chloro-6-(trifluoromethyl)benzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Product 1

HCID 59054583(R)-2-(3-chloro-5-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Procedure

Following the 5a synthetic method, using 3-chloro-5-fluorobenzo[b]thiophene-2-carbonyl chloride (62.27 mg, 0.25 mmol) instead of 5 gave 12a as a white powder; (82.6 mg, 91.7%). [α]D25: −16.8 (c=0.16, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.10-8.06 (m, 1H), 7.81 (d, J=6.9, 1H), 7.61-7.57 (m, 1H), 7.46-7.28 (m, 6H), 5.03-4.97 (m, 1H), 3.45-3.26 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.51, 163.02, 159.79, 138.08, 136.67, 135.36, 133.43, 129.49, 128.39, 126.88, 125.28, 118.22, 116.80, 116.46, 108.25, 107.92, 54.15, 36.79; HRMS (ESI): calcd for: C18H13ClFNO3S [M−H]−=376.0216, obsd [M−H]−=376.0200.

Sources & evidence

ORD record
ord-345b06ad16fd4394995a234c118ecbc9
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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