tert-butyl (2S)-2-amino-3-phenylpropanoate → HCID 59054577, compound

HRID 1479902Notes

Reaction equation

HRID 1479902 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][C:22]([CH3:25])=[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]([CH3:25])=[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 70598307HCID 70598307, compound

Product 1

HCID 59054577HCID 59054577, compound

Procedure

Following the 2a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 2b white powder; (179.63 mg, 96.1%). [α]D25: +23.9 (c=0.29, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 7.76-7.72 (m, 3H), 7.39-7.22 (m, 6H), 5.04-4.98 (m, 1H), 3.44-3.26 (m, 2H), 2.48 (s, 3H); 13C NMR (300 MHz, acetone-d6): δ 171.81, 159.86, 138.26, 138.03, 136.71, 134.63, 131.56, 129.53, 128.38, 127.49, 126.86, 122.53, 122.49, 118.80, 54.13, 36.88, 20.75; HRMS (ESI): calcd for: C19H16ClNO3S [M−H]−=372.0467, obsd [M−H]−=472.0475.

Sources & evidence

ORD record
ord-32a3ac9fe8d443c398d129cbdf632b78
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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