tert-butyl (2S)-2-amino-3-phenylpropanoate → (S)-2-(3-chloro-5-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

HRID 1479917Notes

Reaction equation

HRID 1479917 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=[C:23]([F:25])[CH:22]=[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]=[C:23]([F:25])[CH:22]=[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 59054583(R)-2-(3-chloro-5-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Product 1

HCID 68174283(S)-2-(3-chloro-5-fluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Procedure

Following the 12a synthetic method, using B1 (55.33 mg, 0.25 mmol) instead of A1 gave 12b as a white powder; (87.65 mg, 92.8%). [α]D25: +22.3 (c=0.29, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.11-8.06 (m, 1H), 7.81 (d, J=7.2, 1H), 7.61-7.57 (m, 1H), 7.46-7.22 (m, 6H), 5.03-4.97 (m, 1H), 3.40-3.26 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.50, 163.02, 159.80, 138.09, 136.66, 135.36, 133.46, 129.49, 128.39, 126.88, 125.29, 118.28, 116.80, 116.46, 108.25, 107.93, 54.14, 36.79; HRMS (ESI): calcd for: C18H13ClFNO3S [M−H]−=376.0216, obsd [M−H]−=376.0221.

Sources & evidence

ORD record
ord-035423086087498da366781bfe521cf3
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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