Sodium Bicarbonate → N-[(1,1-Dimethylethoxy)carbonyl]-4-fluoro-L-phenylalanine methyl ester

HRID 571452Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Sn](CCCC)(CCCC)CCCC)=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)(O)[O-].[Na+].[F:39]C(F)(F)S([O-])(=O)=O.[Na+].F[P-](F)(F)(F)(F)F.F[P-](F)(F)(F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>CC(C)=O.[Ag]=O>[CH3:1][O:2][C:3](=[O:33])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:39])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

Conditions

Temperature: 65 °C

Procedure

To N-Boc-4-(Tributylstannyl)-L-phenylalanine Methyl Ester (56.9 mg, 0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23° C. was added silver oxide (1.16 mg, 0.00500 mmol, 0.05 equiv), sodium bicarbonate (16.8 mg, 0.200 mmol, 2.00 equiv), sodium trifluoromethanesulfonate (17.2 mg, 0.100 mmol, 1.00 equiv) and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) (2) (70.5 mg, 0.150 mmol, 1.50 equiv). The reaction mixture was stirred for 5 h at 65° C. in a sealed vial, then cooled to 23° C. and concentrated in vacuo. The residue was purified by preparative TLC with hexane/EtOAc 5:1 (v/v) to afford 25.2 mg of the title compound as a white solid (85% yield).

Workup

temperaturethen cooled to 23° C.
concentrationconcentrated in vacuo
customThe residue was purified by preparative TLC with hexane/EtOAc 5:1 (v/v)

Sources & evidence

ORD record: ord-cf3a5ed8b38e4afebbf00b313db7b471
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024093B2

Reaction notes

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