Triethylamine → HCID 25028946, compound

HRID 1436363Notes

Reaction equation

HRID 1436363 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([NH:13][C@H:14]([CH2:17][CH3:18])[CH2:15][OH:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:13]3[C@H:14]([CH2:17][CH3:18])[CH2:15][O:16][C:27]3=[O:29])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 86618576HCID 86618576, compound

Product 1

HCID 25028946HCID 25028946, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(2R)-2-{[4-(4-bromophenyl)-1,3-thiazol-2-yl]amino}butan-1-ol (2.80 g, 8.56 mmol), prepared in the previous step, and triethylamine (10.5 mL, 60 mmol) in dry dichloromethane (75 mL) was cooled to 0° C. under a nitrogen atmosphere. Triphosgene (5.90 g, 20 mmol) in dry dichloromethane (25 mL) was then added drop wise. After 16 h, the mixture was washed with water and dried (anhydrous MgSO4). The crude product was recrystallized from diethyl ether to afford (4R)-3-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-4-ethyl-1,3-oxazolidin-2-one (1.46 g, 4.1 mmol). mp 134-135° C.; [α]D25=−46° (c=0.0107 g/mL, DMSO); MS (ES) m/z 353.0; HPLC purity 100% at 210-370 nm, 10.8 min; 100% at 270 nm, 10.8 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min. Anal. Calcd for C14H13BrN2O2S: C, 47.60; H, 3.71; N, 7.93. Found: C, 47.45; H, 3.43; N, 7.74.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried (anhydrous MgSO4)
  3. customThe crude product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-0632bebe2a4b43ecbfd1c19e8910eda5
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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