Triethylamine → HCID 25029874, compound

HRID 1436401Notes

Reaction equation

HRID 1436401 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([NH:7][C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)[N:12]=1)[CH2:5][OH:6].C(N(CC)CC)C.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[N:12]=[C:8]([N:7]3[C@H:4]([C:3]([O:2][CH3:1])=[O:20])[CH2:5][O:6][C:29]3=[O:31])[S:9][CH:10]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 86618603HCID 86618603, compound

Product 1

HCID 25029874HCID 25029874, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-[4-(4-Bromophenyl)-1,3-thiazol-2-ylamino]-3-hydroxy-propionic acid methyl ester (1.1 g, 3.08 mmol), prepared in the previous step, was dissolved in 40 mL of methylene chloride and triethylamine (4.3 mL, 30.8 mmol) was added. The mixture was cooled to 0° C. and triphosgene (2.3 g, 7.7 mmol) was added. The mixture was stirred for 1 h and then diluted with methylene chloride, washed with saturated NaHCO3, water, and brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Flash chromatography (gradient 2% acetone/hexane to 15% acetone/hexane) afforded the title compound (510 mg, 44%) as a white solid. mp 165-167° C. HRMS: calcd for C14H, BrN2O4S+H+, 382.96956; found (ESI, [M+H]+), 382.9718. Analytical HPLC: retention time 9.9 min, 210-370 nm the Xterra® RP18 column, 3.5μ, 150×4.6 mm 40° C. 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min, 1.2 mL/min 5 μL injection.

Workup

  1. washwashed with saturated NaHCO3, water, and brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-487d6a60d6944c468210ce14ac5ef7c2
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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