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

HRID 1479919Notes

Reaction equation

HRID 1479919 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([NH:12][C@H:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([OH:16])=[O:15])=[O:11])[S:7][C:6]=2[CH:24]=1.C(OC(=O)[C@H](CC1C=CC=CC=1)N)(C)(C)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([NH:12][C@@H:13]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([OH:16])=[O:15])=[O:11])[S:7][C:6]=2[CH:24]=1

Participants

3

Reactant 2

HCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateHCID 59054584(R)-2-(6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Product 1

HCID 68174316(S)-2-(6-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Procedure

Following the 13a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 13b as colorless oil; (154.68 mg, 90.1%). [α]D25: +15.7 (c=0.26, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.08 (d, J=8.1 Hz, 1H), 8.03 (s, 1H), 7.96-7.91 (m, 1H), 7.80-7.76 (m, 1H), 7.39-7.18 (m, 6H), 4.98-4.92 (m, 1H), 3.36-3.15 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 172.17, 163.11, 161.48, 159.86, 142.28, 139.43, 137.51, 136.19, 129.23, 128.32, 126.89, 126.76, 126.60, 124.43, 114.09, 108.67, 54.12, 37.02; HRMS (ESI): calcd for: C18H14FNO3S [M−H]−=342.0606, obsd [M−H]−=342.0593.

Sources & evidence

ORD record
ord-38d11c888351452db1610d7bcd694630
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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