Hydrochloric Acid → HCID 86705560, compound

HRID 2279574Notes

Reaction equation

HRID 2279574 reaction equation
[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]([NH:16][S@](C(C)(C)C)=O)[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1.[ClH:24].O1CCOCC1>CO.C(Cl)Cl>[ClH:24].[NH2:16][C@@H:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH:2]([F:1])[F:23])=[CH:5][CH:6]=1)[CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86705559HCID 86705559, compound

Product 1

HCID 86705560HCID 86705560, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 380 (8.98 g, 25.7 mmol) in MeOH (60 mL) and DCM (30 mL) was added 4M HCl in dioxane (12.9 mL, 51.4 mmol) and stirring was continued for 60 min at RT. HCl was removed with a stream of dry N2 and most of the solvent was removed on in a rotary evaporator. Ether was added to the residue and the precipitated white solid was filtered to afford 7.23 g (100%) of (R)-methyl 3-amino-3-(4-(difluoromethoxy)phenyl)propanoate hydrochloride (382) which was ca. 95% ee by chiral hplc.

Workup

  1. customHCl was removed with a stream of dry N2 and most of the solvent
  2. customwas removed on in a rotary evaporator
  3. additionEther was added to the residue
  4. filtrationthe precipitated white solid was filtered

Sources & evidence

ORD record
ord-d78fef4cf3bd4f418f7ca6b0cbba4728
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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