Hydrochloric Acid → HCID 57539219, compound

HRID 601960Notes

Reaction equation

HRID 601960 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:9]([CH2:14][O:15][CH:16]([F:18])[F:17])[C:10]([O:12]C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].Cl>C1COCC1.C(OCC)(=O)C>[CH2:19]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]([CH2:14][O:15][CH:16]([F:18])[F:17])[C:10]([OH:12])=[O:11])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57539220HCID 57539220, compound

Product 1

HCID 57539219HCID 57539219, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-dibenzylamino-3-difluoromethoxy-propionate (1.2 g, 3.43 mmol) was stirred with 1N LiOH (10.3 mL, 10.3 mmol) in THF (40 mL) at 50° C. for 2 hours and then stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and acidified with 1N HCl. The organic layer was dried with sodium sulfate and concentrated with silica gel. The product was purified by column chromatography, eluting with 10-50% ethyl acetate in hexanes, to give 2-(dibenzylamino)-3-(difluoromethoxy)propanoic acid (730 mg, 63.5%) as a white solid. 1H NMR (300 MHz, CDCl3): δ(ppm) 7.26-7.42 (m, 10H), 6.29 (bt, 1H), 4.45 (dd, 1H), 4.28 (dd, 1H), 3.94 (q, 4H) and 3.85 (m, 1H).

Workup

  1. dry with materialThe organic layer was dried with sodium sulfate
  2. concentrationconcentrated with silica gel
  3. customThe product was purified by column chromatography
  4. washeluting with 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1a3574d6a6a940078754b7ab80759eed
Source dataset
uspto-grants-2011_03
Patent number
US07902401B2

Reaction notes

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