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

HRID 1479905Notes

Reaction equation

HRID 1479905 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][C:22]([F:25])=[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]([F:25])=[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 53242268N-[(3-Chloro-6-fluorobenzo[b]thien-2-yl)carbonyl]-D-phenylalanine

Product 1

HCID 59054572(S)-2-(3-chloro-6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Procedure

Following the 4a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 4b as a white powder; (175.31 mg, 92.8%). [α]D25: +15.5 (c=0.38, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.03-7.77 (m, 3H), 7.44-7.25 (m, 6H), 5.03-4.97 (m, 1H), 3.45-3.26 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 163.90, 160.62, 159.50, 139.01, 136.65, 133.57, 129.50, 128.40, 126.88, 124.94, 115.15, 114.82, 109.31, 108.96, 54.06, 36.79; HRMS (ESI): calcd for: C18H13ClFNO3S [M+H]+=378.0361, obsd [M+H]+=378.0352.

Sources & evidence

ORD record
ord-5023eb8b6b7e4e4498feab8cbebc6b27
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

Loading…