1,2-Dichloroethane → (S)-4-(benzyloxycarbonylamino)-1-oxo-1-(perfluorophenoxy)butan-2-yl benzoate

HRID 1949610Notes

Reaction equation

HRID 1949610 reaction equation
[C:1]([O:9][C@@H:10]([CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:27][C:28]1[C:33](O)=[C:32]([F:35])[C:31]([F:36])=[C:30]([F:37])[C:29]=1[F:38].C(Cl)CCl>CN(C=O)C>[C:1]([O:9][C@@H:10]([CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[C:11](=[O:13])[O:12][C:33]1[C:32]([F:35])=[C:31]([F:36])[C:30]([F:37])=[C:29]([F:38])[C:28]=1[F:27])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 58503128(S)-2-(benzoyloxy)-4-(benzyloxycarbonylamino)butanoic acid

Product 1

HCID 58503143(S)-4-(benzyloxycarbonylamino)-1-oxo-1-(perfluorophenoxy)butan-2-yl benzoateYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of (S)-2-(benzoyloxy)-4-(benzyloxycarbonylamino)butanoic acid (2, 196 g, 0.548 mol) and pentafluorophenol (111 g, 0.603 mol) in 1.3 L DMF at 0° C. was added EDC (126 g, 0.658 mol) and the reaction was stirred overnight. The reaction mixture was diluted with hexanes:EtOAc (1.5 L, 1:1) and with brine/water (1 L, 1:1), and the organic layer was separated and washed with 1 M citric acid (3×600 mL), followed by sat. NaHCO3:1M NaOH (3×500 mL, 1:1) and brine (500 mL). The organic layer was dried over MgSO4, filtered and concentrated under vacuum to yield (S)-4-(benzyloxycarbonylamino)-1-oxo-1-(perfluorophenoxy)butan-2-yl benzoate (3, 255 g, 88% yield) as a white waxy solid that was used in the next step without further purification.

Workup

  1. customEtOAc (1.5 L, 1:1) and with brine/water (1 L, 1:1), and the organic layer was separated
  2. washwashed with 1 M citric acid (3×600 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-88918e5101184780a7d769eed0a22800
Source dataset
uspto-grants-2013_03
Patent number
US08399419B2

Reaction notes

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