Triethylamine → HCID 25029410, compound

HRID 1436438Notes

Reaction equation

HRID 1436438 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:13][C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)[N:18]=1)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:11][O:12][C:34](=[O:36])[N:13]1[C:14]1[S:15][CH:16]=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=2)[N:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 86618616HCID 86618616, compound

Product 1

HCID 25029410HCID 25029410, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(R)-3-Benzyloxy-2-[4-(4-bromo-phenyl)-thiazol-2-ylamino]-propan-1-ol (110 mg, 0.26 mmol), prepared in the previous step, was dissolved in methylene chloride (10 mL), cooled to 0° C. and triethylamine (0.36 mL, 2.6 mmol) was added followed by triphosgene (0.19 g, 0.65 mmol). The mixture was stirred for 3 h, diluted with methylene chloride and washed with saturated NaHCO3, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (10% acetone in hexane) afforded the title compound (35 mg, 30%). HRMS: calcd for C20H17BrN2O3S+H+, 445.02160; found (ESI, [M+H]+), 445.0201; Analytical HPLC: purity 100% at 210-370 nm, 11.1 min; 93.8% at 238 nm, 11.1 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.

Workup

  1. washwashed with saturated NaHCO3, brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c528bdd217644117af519be836242059
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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