Diisopropylethylamine → HCID 68076180, compound

HRID 929952Notes

Reaction equation

HRID 929952 reaction equation
[NH2:1][CH:2]([CH3:10])[CH:3]([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)[OH:4].C(N(C(C)C)CC)(C)C.Cl[C:21](Cl)([O:23]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH3:10][C@H:2]1[C@H:3]([C:5]2[S:6][CH:7]=[CH:8][N:9]=2)[O:4][C:21](=[O:23])[NH:1]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 45121875HCID 45121875, compound

Product 1

HCID 68076180HCID 68076180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of diastereoisomers of 2-amino-1-thiazol-2-yl-propan-1-ol (4.20 g, 18.2 mmol) was dissolved in 160 mL of CH2Cl2. Diisopropylethylamine (11.1 mL, 63.6 mmol) was added at 0° C., followed by triphosgene (2.70 g, 9.09 mmol) dissolved in 40 mL of CH2Cl2. The reaction mixture was stirred at room temperature for 2 hours and then diluted with CH2Cl2. The organic solvents were separated, washed with aqueous NaHCO3 and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (80 g SiO2) using EtOAc in hexane from 0% to 100 in order to give the title compound as a single enantiomer (2.16 g, 64%). LC-MS: [M+H] 185.3; Rt 0.45 min; (LCMS method 1). 1H NMR (400 MHz, CHCl3-d): 7.75 (d, 1H), 7.35 (d, 1H), 5.60 (br s, 1H), 5.32 (d, 1H), 4.18-4.09 (m, 1H), 1.45 (d, 3H).

Workup

  1. customThe organic solvents were separated
  2. washwashed with aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (80 g SiO2)

Sources & evidence

ORD record
ord-80e58bd5dc0c45cbba07791a20b0fa99
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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