tert-butyl (2S)-2-amino-3-phenylpropanoate → (S)-2-(3-chloro-5,6-difluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

HRID 1479911Notes

Reaction equation

HRID 1479911 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=[C:23]([F:25])[C:22]([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]=[C:23]([F:25])[C:22]([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]

Participants

3

Reactant 2

HCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateHCID 59054581(R)-2-(3-chloro-5,6-difluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Product 1

HCID 68173579(S)-2-(3-chloro-5,6-difluorobenzo[b]thiophene-2-carboxamido)-3-phenylpropanoic acid

Procedure

Following the 8a synthetic method, using B1 (55.33 mg, 0.25 mmol) instead of A1 gave 8b as a white powder; (93.51 mg, 94.5%). [α]D25: +22.3 (c=0.43, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.80 (s, 1H), 7.64-7.51 (m, 3H), 7.34-7.24 (m, 5H), 5.16-5.10 (m, 1H), 3.43-3.28 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 175.44, 160.03, 153.01, 151.93, 149.64, 148.62, 135.14, 133.75, 133.28, 129.45, 128.83, 127.55, 188.89, 110.98, 110.79, 110.53, 54.04, 37.28; HRMS (ESI): calcd for: C18H12ClF2NO3S [M−H]−=394.0122, obsd [M−H]−=394.0127.

Sources & evidence

ORD record
ord-545316b65e114641be41945d5e926a7f
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

Loading…