3-Chloro-5,6-difluoro-1-benzothiophene-2-carbonyl chloride → (R)-2-(3-chloro-5,6-difluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

HRID 1479910Notes

Reaction equation

HRID 1479910 reaction equation
ClC1C2C=CC(C(F)(F)F)=CC=2SC=1C([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.[Cl:29][C:30]1[C:31]2[CH:41]=[C:40]([F:42])[C:39]([F:43])=[CH:38][C:32]=2[S:33][C:34]=1[C:35](Cl)=[O:36]>>[Cl:29][C:30]1[C:31]2[CH:41]=[C:40]([F:42])[C:39]([F:43])=[CH:38][C:32]=2[S:33][C:34]=1[C:35]([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:36]

Participants

3

Reactant 2

HCID 110328263-Chloro-5,6-difluoro-1-benzothiophene-2-carbonyl chlorideHCID 70558597(R)-2-(3-chloro-6-(trifluoromethyl)benzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Product 1

HCID 59054581(R)-2-(3-chloro-5,6-difluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Procedure

Following the 5a synthetic method, using 5-2 (66.77 mg, 0.25 mmol) instead of 5 gave 8a as a white powder; (91.63 mg, 92.6%). [α]D25: −15.9 (c=0.19, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.91 (s, 1H), 7.63-7.52 (m, 3H), 7.37-7.25 (m, 5H), 5.16-5.09 (m, 1H), 3.43-3.28 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 175.39, 160.02, 152.99, 151.92, 149.63, 148.61, 135.17, 133.75, 133.25, 129.45, 128.82, 127.53, 118.84, 110.98, 110.77, 110.50, 54.05, 37.28; HRMS (ESI): calcd for: C18H12ClF2NO3S [M−H]−=394.0122, obsd [M−H]−=394.0137.

Sources & evidence

ORD record
ord-bf6f6312c384411f945cbf5e67f9d68f
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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