Dimethylformamide → HCID 90132496, compound

HRID 2275805Notes

Reaction equation

HRID 2275805 reaction equation
[NH2:1][CH2:2][CH:3]([OH:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([F:13])[CH:7]=1.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(N(CC)C(C)C)(C)C.CN(C=O)C>C1COCC1.CN(C)C1C=CN=CC=1>[F:13][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[F:12])[O:5][CH2:4][CH:3]([OH:14])[CH2:2][NH:1][C:16](=[O:17])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 43554746HCID 43554746, compound

Product 1

HCID 90132496HCID 90132496, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1 of rac-1-amino-3-(3,4-difluorophenoxy)propan-2-ol (4.9 mmol, 1 equivalent) was dissolved in 16 ml of THF, and 0.76 ml of benzyl chloroformate (0.9 g, 5.4 mmol, 1.1 equivalents) and then 2.6 ml of N,N-diisopropylethylamine (1.9 g, 14.8 mmol, 3 equivalents) and 0.12 g of 4-dimethylaminopyridine were added. The mixture was stirred at RT for 30 min. 2 ml of DMF were then added, and the mixture was stirred at RT overnight. The mixture was concentrated and the residue was then taken up in ethyl acetate. The organic phase was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated. This gave 2.2 g (96% of theory, purity 73%) as a crude product which was reacted without further purification.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. concentrationThe mixture was concentrated
  3. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis gave 2.2 g (96% of theory, purity 73%) as a crude product which was reacted without further purification

Sources & evidence

ORD record
ord-9c79678f6e6b47e79cb8132cc6adf5ec
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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