Methyl iodide → (+-)-(R/S)-2-tert-Butoxycarbonylamino-3-(4-iodo-phenyl)-propionic acid methyl ester

HRID 1782670Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:21]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:21][O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-tert-butoxycarbonylamino-3-(4-iodophenyl)-propanoic acid (5.0 g, 12.8 mmol) in DMF (50 mL) was treated with K2CO3 (2.2 g, 15.4 mmol). After stirring for 15 min, the solution was cooled to 0° C. and treated with iodomethane (1.0 mL, 15.4 mmol) After the addition was complete, the reaction mixture was stirred at room temperature for another 16 h, filtered and the resulting solid was washed with ethyl acetate (200 mL). The filtrate was washed successively with 5% aq HCl, sat. aq NaCl, dried over MgSO4 and concented. Purification by flash column chromatography (5% ethyl acetate in heptane) provided the desired product (5.74 g, 98%) as an oil. 1H NMR (CDCl3), δ 7.61 (d, J=9 Hz, 2 H), 7.74 (d, J=9, 2H), 4.97 (d, J=7 Hz, 1 H), 4.56 (m, 1 H), 3.73 (s, 3 H), 3.02 (ddd, J=7, 7, 12 Hz, 2 H), 1.47 (s, 9 H)

Workup

additionAfter the addition
stirringthe reaction mixture was stirred at room temperature for another 16 h
filtrationfiltered
washthe resulting solid was washed with ethyl acetate (200 mL)
washThe filtrate was washed successively with 5% aq HCl, sat. aq NaCl
dry with materialdried over MgSO4
customPurification by flash column chromatography (5% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-c4a20bd2579a469cb008df46655d2422
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498356B2

Reaction notes

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