Chloride → HCID 86590271, compound

HRID 1515120Notes

Reaction equation

HRID 1515120 reaction equation
O1[CH2:6][CH2:5]OCC1.[ClH:7].[CH3:8][O:9][C:10](=[O:36])[C@@H:11]([NH:28][C:29](OC(C)(C)C)=[O:30])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:24](=[O:25])[CH:23]=[CH:22][N:21]([CH3:26])[C:20]2=[O:27])=[CH:15][CH:14]=1.[Cl-:37]>C(N(CC)CC)C.CN(C)C=O>[CH3:8][O:9][C:10](=[O:36])[C@@H:11]([NH:28][C:29](=[O:30])[C:6]1[C:5]([Cl:7])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:37])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:24](=[O:25])[CH:23]=[CH:22][N:21]([CH3:26])[C:20]2=[O:27])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86590272HCID 86590272, compound

Product 1

HCID 86590271HCID 86590271, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

6 ml of dioxan solution including 4N hydrogen chloride was added to 86 mg of (2S)-2-(t-butoxycarbonylamino)-3-[4-(1-methyluracil-3-yl)phenyl] propionic acid methylester and stirred for 1 hour. 10 ml of dimethylformamide, 62 μl of triethylamine and 34 μl of 2,6-dichloromenzoyl chloride were added to the residual material obtained by removing the solvent and stirred for 30 minutes. The reaction solvent was diluted by ethyl acetate, washed with 1N hydrochloric acid, an aqueous solution of saturated sodium hydrogen carbonate and saturated NaCl aqueous solution, and dried with magnesium sulfate and the solvent was removed to obtain a crude material of the title compound. The crude material was purified by reverse phase HPLC to obtain the title compound (26 mg).

Workup

  1. customobtained
  2. customby removing the solvent
  3. stirringstirred for 30 minutes
  4. additionThe reaction solvent was diluted by ethyl acetate
  5. washwashed with 1N hydrochloric acid
  6. dry with materialan aqueous solution of saturated sodium hydrogen carbonate and saturated NaCl aqueous solution, and dried with magnesium sulfate
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-c0bd62799a5747148b387bab1810f513
Source dataset
uspto-grants-2012_07
Patent number
US08222405B2

Reaction notes

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