Methanol → Methyl (2S)-2-amino-3-(4-iodophenyl)propanoate hydrochloride

HRID 1664107Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].S(Cl)([Cl:16])=O.[CH3:18]O>>[ClH:16].[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([I:13])=[CH:11][CH:12]=1)[C:3]([O:5][CH3:18])=[O:4]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 1344974-Iodophenylalanine

Product 1

HCID 67437706Methyl (2S)-2-amino-3-(4-iodophenyl)propanoate hydrochlorideYield 99%

Procedure

To a solution of 92 (2.00 g, 6.87 mmol) in MeOH (10 mL) at 0° C. was added thionyl chloride (2 mL) and the resulting solution was allowed to stir for 16 h whilst equilibrating to RT. The reaction was evaporated to dryness in vacuo to yield the title compound (2.25 g, 6.80 mmol, 99%) as a white solid, which had spectral data in agreement with that reported.93 [α]D21 −9.3 (c. 0.15, HCl). Mp 195-198° C. (lit. 199.5-200.5° C.)93 1H NMR (CD3OD, 300 MHz): δ 7.72 (d, J=8.4 Hz, 2H, ArH2′ and ArH6′); 7.06 (d, J=8.4 Hz, 2H, ArH3′ and ArH5′); 4.33 (dd, J=6.3, 6.9 Hz, 1H, H2); 3.80 (s, 3H, OCH3); 3.23 (dd, J=6.6, 14.4 Hz, 1H, H3a); 3.15 (dd, J=7.2, 14.4 Hz, 1H, H3b). Mass Spectrum (ES, +ve) m/z 306 (100%) [M+]. HRMS calcd for C10H13INO2 305.9986 found 305.9980.

Workup

customThe reaction was evaporated to dryness in vacuo

Sources & evidence

ORD record: ord-717f5235a478477a9623caa5f2f8b5d6
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039430B2

Reaction notes

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