tert-butyl (2S)-2-amino-3-phenylpropanoate → HCID 68174272, compound

HRID 1479908Notes

Reaction equation

HRID 1479908 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[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]=[CH:23][C:22]([O:25][CH3:26])=[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 59054457HCID 59054457, compound

Product 1

HCID 68174272HCID 68174272, compound

Procedure

Following the 6a synthetic method, using B1 (55.33 mg, 0.25 mmol) instead of A1 gave 6b as a white powder; (88.78 mg, 91.1%). [α]D25: +16.5 (c=0.29, CHCl3); 1H-NMR (300 MHz, CDCl3): δ 8.79 (s, 1H), 7.68 (d, J=9.0 Hz, 1H), 7.59 (d, J=7.2 Hz, 1H), 7.34-7.23 (m, 6H), 7.07 (dd, J=2.4, 9.0 Hz, 1H), 5.18-5.12 (m, 1H), 3.89 (s, 3H), 3.43-3.28 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 175.50, 160.91, 159.94, 140.08, 135.36, 132.54, 130.83, 129.51, 128.97, 128.76, 127.41, 124.12, 119.87, 116.45, 113.99, 104.31, 55.71, 54.06, 37.36; HRMS (ESI): calcd for: C19H16ClNO4S [M−H]−=388.0416, obsd [M−H]−=388.0402.

Sources & evidence

ORD record
ord-e64518a3982d4c2ca04bdeddc2791ab3
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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