HCID 57539221, compound → HCID 57539232, compound

HRID 2096918Notes

Reaction equation

HRID 2096918 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): (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-3168f2e0bd8d46a2bc121e5ab54dcde6
Source dataset
uspto-grants-2013_05
Patent number
US08450336B2

Reaction notes

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