tert-butyl (2S)-2-amino-3-phenylpropanoate → (S)-2-(3-chloro-6-(trifluoromethyl)benzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

HRID 1479907Notes

Reaction equation

HRID 1479907 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[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].C(OC(=O)[C@H](CC1C=CC=CC=1)N)(C)(C)C>>[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[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 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateHCID 70558597(R)-2-(3-chloro-6-(trifluoromethyl)benzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Product 1

HCID 59054579(S)-2-(3-chloro-6-(trifluoromethyl)benzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acidYield 93.1%

Procedure

Following the 5a synthetic method, using B1 (55.33 mg, 0.25 mmol) instead of A1 gave 5b as a yellow powder (99.57 mg, 93.1%). [α]D25: +24.7 (c=0.36, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 8.09 (s, 1H), 7.90 (d, J=8.7 Hz, 1H), 7.69-7.61 (m, 2H), 7.36-7.25 (m, 5H), 7.04 (s, 1H), 5.15-5.13 (m, 1H), 3.44-3.29 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 175.32, 160.09, 139.05, 137.72, 135.22, 135.18, 129.87, 129.45, 128.83, 127.53, 125.62, 123.85, 122.14, 120.43, 120.37, 119.48, 54.20, 37.26, 29.70; HRMS (ESI): calcd for: C19H13ClF3NO3S [M−H]−=426.0184, obsd [M−H]−=426.0180.

Sources & evidence

ORD record
ord-3f1e29c762474e8289cb9ba196e384ab
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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