HCID 57539221, compound → HCID 57539232, compound

HRID 601970Notes

Reaction equation

HRID 601970 reaction equation
C([N:8](CC1C=CC=CC=1)[C@H:9]([CH2:20][O:21][CH:22]([F:24])[F:23])[C:10]([O:12]CC1C=CC=CC=1)=[O:11])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:8][C@H:9]([CH2:20][O:21][CH:22]([F:24])[F:23])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 57539221HCID 57539221, compound

Product 1

HCID 57539232HCID 57539232, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Benzyl (2R) 2-dibenzylamino-3-difluoromethoxy-propionate (3.1 g, 6.28 mmol) was stirred with Pd(OH)2 in methanol under H2 overnight. The reaction mixture was filtered and the filtrate concentrated to dryness, then triturated with diethyl ether to give (2R)-2-amino-3-(difluoromethoxy)propanoic acid (773 mg, 68.4%) as a white solid. 1H NMR (300 MHz, MeOD): δ(ppm) 6.49 (wt, 1H), 4.33 (dd, 1H), 4.22 (dd, 1H), and 3.88 (dd, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated to dryness
  3. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-e06b643ae79548a7903976fcdfa790c8
Source dataset
uspto-grants-2011_03
Patent number
US07902401B2

Reaction notes

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