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Monobasic potassium phosphate → HCID 7091053, compound

HRID 339818
Notes
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Reaction equation

HRID 339818 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][CH:6]([NH2:15])[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[F:14])C.P([O-])(O)(O)=O.[K+]>O>[NH2:15][C@H:6]([C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[F:14])[CH2:5][C:4]([OH:16])=[O:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 516951Monobasic potassium phosphateHCID 43312570Ethyl 3-amino-3-(2,5-difluorophenyl)propanoate

Product 1

HCID 7091053HCID 7091053, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-Amino-3-(2,5-difluorophenyl)propionic acid ethyl ester (3 g) was emulsified in water (pH=9.2) and admixed with potassium dihydrogenphosphate (5 mg) (pH=8.5). After addition of Amano Lipase PS (150 mg), the mixture was stirred overnight. The pH remains at 7.5. The mixture was then admixed with water (30 ml) and filtered through kieselguhr and washed several more times with water. The aqueous phase was then extracted with dichloromethane (3×30 ml), and the organic phase was dried (Na2SO4) and concentrated. This gave the product (1.3 g) with an ee=90% by HPLC.

Workup

  1. additionAfter addition of Amano Lipase PS (150 mg)
  2. filtrationfiltered through kieselguhr
  3. washwashed several more times with water
  4. extractionThe aqueous phase was then extracted with dichloromethane (3×30 ml)
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-50215cbfa0844d518cd67d540ea07104
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895547B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes