tert-butyl (2S)-2-amino-3-phenylpropanoate → HCID 25625244, compound

HRID 1479914Notes

Reaction equation

HRID 1479914 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]2[S:6][C:7]([C:9]([NH:11][C@H:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]([OH:15])=[O:14])=[O:10])=[CH:8][C:4]=2[CH:3]=1.C(OC(=O)[C@H](CC1C=CC=CC=1)N)(C)(C)C>>[F:1][C:2]1[CH:24]=[CH:23][C:5]2[S:6][C:7]([C:9]([NH:11][C@@H:12]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:13]([OH:15])=[O:14])=[O:10])=[CH:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoateHCID 25625240HCID 25625240, compound

Product 1

HCID 25625244HCID 25625244, compound

Procedure

Following the 10a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 10b as a white powder; (163.96 mg, 95.5%). [α]D25: +21.8 (c=0.35, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 7.97 (s, 1H), 7.74-7.69 (m, 1H), 7.60 (s, 1H), 7.39-7.16 (m, 7H), 6.86 (d, J=7.5 Hz, 1H), 5.09-5.07 (m, 1H), 3.39-3.22 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 175.03, 162.49, 162.17, 159.27, 139.84, 139.51, 136.42, 135.52, 129.37, 128.76, 127.36, 125.57, 124.05, 115.93, 110.45, 53.87, 37.31; HRMS (ESI): calcd for: C18H14FNO3S [M−H]−=342.0606, obsd [M−H]−=342.0596.

Sources & evidence

ORD record
ord-c668a5fb7ad445e6ae952eb35e903d03
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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