Benzyl Alcohol → Benzyl 2-amino-3-(3-hydroxyphenyl)propanoate

HRID 2403243Notes

Reaction equation

[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)Cl.[CH:13]1[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]([CH2:20][C@H:21]([NH2:25])[C:22](O)=[O:23])[CH:14]=1>CCOC(C)=O>[NH2:25][CH:21]([CH2:20][C:15]1[CH:14]=[CH:13][CH:18]=[C:17]([OH:19])[CH:16]=1)[C:22]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:23]

Participants

Conditions

Temperature: -5 °C

Procedure

To 10 mL of benzyl alcohol at −5° C. was added, with stirring, 0.2 mL of SOCl2 slowly. The clear colorless solution was cooled to −5° C. and 490 mg of meta-Tyrosine was added. After 5 min, the resulting solution was heated to 120° C. overnight. 100 ml of AcOEt are added. The organic phase are washed with saturated NaHCO3 and brine then dried over Na2SO4, filtered and concentrated to afford 170 as a white solid (430 mg, 59%). 1H NMR (DMSO): δ 1.90 (s, 3H), 2.87 (dd, 1H, J=13.1, 6.5 Hz), 2.94 (dd, 1H, J=13.1, 6.5 Hz), 3.73 (t, 1H, J=6.5 Hz), 5.19 (s, 2H), 6.70 (d, 1H, J=7.7 Hz), 6.75 (s, 1H), 7.17 (t, 1H, J=7.7 Hz), 7.41 (d, 1H, J=7.0 Hz), 7.48 (m, 5H), 9.37 (s, 1H).

Workup

temperaturethe resulting solution was heated to 120° C. overnight
washThe organic phase are washed with saturated NaHCO3 and brine
dry with materialthen dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-709e1b3ac37e4414a0b30ab88b981d87
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802666B2

Reaction notes

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