Water → HCID 58706654, compound

HRID 1716512Notes

Reaction equation

HRID 1716512 reaction equation
Cl.Cl.[NH2:3][C@H:4]([C:7]1[S:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[N:13]=2)=[CH:10][N:11]=1)[CH2:5][OH:6].C(N(CC)CC)C.Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl.O>C(Cl)(Cl)Cl>[Br:18][C:14]1[N:13]=[C:12]([C:9]2[S:8][C:7]([C@@H:4]3[CH2:5][O:6][C:27](=[O:29])[NH:3]3)=[N:11][CH:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 86607642HCID 86607642, compound

Product 1

HCID 58706654HCID 58706654, compoundYield 232.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (S)-2-amino-2-[5-(6-bromopyridin-2-yl)thiazol-2-yl]ethanol dihydrochloride (1.00 g, 2.68 mmol) obtained in Step 3, triethylamine (3.7 ml, 2.68 mmol) in chloroform (15 ml), a solution of triphosgene (278 mg, 0.94 mmol) in chloroform (5 ml) was added dropwise while cooled to −78° C., and the mixture was stirred at the same temperature for 2 hours. The reaction solution was warmed to room temperature and water was added and it was extracted with ethyl acetate. After washed with a saturated brine, the organic layer was dried over magnesium sulfate. After concentrated, the residue was purified by flash chromatography on silica gel (chloroform:methanol:ethyl acetate=15:1:1) and the title compound (712 mg, 82%) was obtained.

Workup

  1. temperatureThe reaction solution was warmed to room temperature
  2. extractionit was extracted with ethyl acetate
  3. washAfter washed with a saturated brine
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationAfter concentrated
  6. customthe residue was purified by flash chromatography on silica gel (chloroform:methanol:ethyl acetate=15:1:1)

Sources & evidence

ORD record
ord-deb53124e6f344bb8891043d343a6d26
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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