Dimethylformamide → HCID 90136031, compound

HRID 2275797Notes

Reaction equation

HRID 2275797 reaction equation
[NH2:1][CH2:2][CH:3]([OH:9])[CH2:4][O:5][CH:6]([CH3:8])[CH3:7].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C(N(C(C)C)CC)(C)C.CN(C=O)C>C1COCC1>[OH:9][CH:3]([CH2:4][O:5][CH:6]([CH3:8])[CH3:7])[CH2:2][NH:1][C:11](=[O:12])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 6623501-Amino-3-isopropoxy-propan-2-ol

Product 1

HCID 90136031HCID 90136031, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g of rac-1-amino-3-isopropoxypropan-2-ol (7.5 mmol, 1 equivalent) were initially charged in 25 ml of THF, and 1.16 ml of benzyl chloroformate (8.3 mmol, 1.1 equivalents), 3.9 ml of diisopropylethylamine (22.5 mmol, 3 equivalents) and 183 mg of N,N-dimethylaminopyridine (1.5 mmol, 0.2 equivalents) were added. The reaction mixture was stirred at RT, and after about 30 min 5 ml of DMF were added. After a further 2.5 h at RT, the mixture was concentrated to dryness. The residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and then with saturated aqueous sodium chloride solution. The organic phase was dried over magnesium sulphate, filtered and concentrated. The residue was used without further purification for the next reaction.

Workup

  1. concentrationthe mixture was concentrated to dryness
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was used without further purification for the next reaction

Sources & evidence

ORD record
ord-01e565fc6cd34823ab50ff6ba55b6e18
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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