3-Chloro-6-fluorobenzo[b]thiophene-2-carbonyl chloride → (R)-2-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid

HRID 1479909Notes

Reaction equation

HRID 1479909 reaction equation
S1C(C([NH:8][C@H:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:10]([OH:12])=[O:11])=O)=CC2C=CC=CC1=2.[Cl:25][C:26]1[C:27]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:28]=2[S:29][C:30]=1[C:31](Cl)=[O:32]>>[Cl:25][C:26]1[C:27]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:28]=2[S:29][C:30]=1[C:31]([NH:8][C@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)[C:10]([OH:12])=[O:11])=[O:32]

Participants

3

Reactant 2

HCID 27831733-Chloro-6-fluorobenzo[b]thiophene-2-carbonyl chlorideHCID 68175096(R)-2-(benzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid

Product 1

HCID 59054580(R)-2-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)-3-(4-hydroxyphenyl)propanoic acid

Procedure

Following the 9a synthetic method, using 3-chloro-6-fluorobenzo[b]thiophene-2-carbonyl chloride (249.09 mg, 1.0 mmol) instead of 3 gave 7a as a colorless oil; (145.32 mg, 36.9%). [α]D25: +18.3 (c=0.37, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.97-7.87 (m, 2H), 7.73 (d, J=6.6 Hz, 1H), 7.45-7.38 (m, 1H), 7.18-7.15 (m, 2H), 6.80-6.77 (m, 2H), 4.96-4.90 (m, 1H), 3.34-3.16 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.56, 163.89, 160.62, 159.45, 156.42, 139.16, 133.55, 130.54, 127.03, 124.94, 118.51, 115.22, 114.80, 109.29, 108.95, 54.14, 35.98; HRMS (ESI): calcd for: C18H13ClFNO4S [M−H]−=392.0165, obsd [M−H]−=392.0174.

Sources & evidence

ORD record
ord-dd2092921f654258950b49eaade0b5a6
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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