tert-butyl (2S)-2-amino-3-phenylpropanoate → HCID 68174277, compound

HRID 1479915Notes

Reaction equation

HRID 1479915 reaction equation
[Cl:1][C:2]1[C:3]2[CH:24]=[CH:23][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]=[CH:23][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 59054582HCID 59054582, compound

Product 1

HCID 68174277HCID 68174277, compound

Procedure

Following the 11a synthetic method, using B1 (110.65 mg, 0.5 mmol) instead of A1 gave 11b as a colorless oil; (164.98 mg, 91.7%). [α]D25: +23.3 (c=0.42, CHCl3); 1H-NMR (300 MHz, acetone-d6): δ 8.06-8.00 (m, 1H), 7.91-7.87 (m, 1H), 7.80 (d, J=6.9 Hz, 1H), 7.62-7.55 (m, 2H), 7.37-7.22 (m, 5H), 5.05-4.98 (m, 1H), 3.45-3.26 (m, 2H); 13C NMR (300 MHz, acetone-d6): δ 171.56, 159.74, 137.75, 136.74, 136.67, 132.78, 129.51, 128.40, 127.67, 126.88, 125.74, 123.03, 122.83, 118.86, 54.09, 36.83; HRMS (ESI): calcd for: C18H14ClNO3S [M−H]−=358.0310, obsd [M−H]−=358.0312.

Sources & evidence

ORD record
ord-d489d242a45d482cb9416583068833c9
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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