Triethylamine → HCID 93962027, compound

HRID 589934Notes

Reaction equation

HRID 589934 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Br:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][C:26]=1[F:34].Cl.[CH3:36][O:37][C:38](=[O:43])[C@H:39]([CH2:41][OH:42])[NH2:40].C(N(CC)CC)C>O.CN(C)C=O>[CH3:36][O:37][C:38](=[O:43])[C@H:39]([CH2:41][OH:42])[NH:40][C:29](=[O:31])[C:28]1[CH:32]=[CH:33][C:25]([Br:24])=[C:26]([F:34])[CH:27]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27733414-Bromo-3-fluorobenzoic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 93962027HCID 93962027, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole monohydrate (839 mg, 5.48 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.05 g, 5.48 mmol) were added to an N,N-dimethylformamide (34 mL) solution of 4-bromo-3-fluorobenzoic acid (1.00 g, 4.57 mmol) at room temperature. The mixture was stirred at the same temperature for 30 minutes, and then L-serine methyl ester hydrochloride (1.42 g, 9.13 mmol) and triethylamine (1.27 mL, 9.13 mmol) were added to the mixture. The resulting mixture was further stirred at the same temperature for 15 minutes. Water was added to the reaction mixture, and the resulting mixture was extracted twice with ethyl acetate. The organic layer thus obtained was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give the crude title compound (1.63 g).

Workup

  1. stirringThe resulting mixture was further stirred at the same temperature for 15 minutes
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. customThe organic layer thus obtained
  4. washwas washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5850dbc46f614edfa09af2d5b43b2e2e
Source dataset
uspto-grants-2016_01
Patent number
US09233958B2

Reaction notes

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