Dichloromethane methanol → HCID 67076752, compound

HRID 1348585Notes

Reaction equation

HRID 1348585 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[N+:22]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClCCl.CO>CO.[Pd]>[NH2:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[O:14][CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 67076913HCID 67076913, compound

Product 1

HCID 67076752HCID 67076752, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4.35 g (S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-2-nitro-phenoxy)-propionic acid in 80 ml methanol were hydrogenated with 0.14 g Pd(10%)/C. Chromatography on silicagel with dichloromethane/methanol 9:1 yielded 2.08 g (52%) (S)-3-(2-amino-4-fluoro-phenoxy)-2-tert-butoxycarbonylamino-propionic acid as light brown solid, MS m/e (%): 313.0 (M−H+, 100).

Sources & evidence

ORD record
ord-0bfc835dd4bf481bb5bf4f5d588b1b6a
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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