HCID 68760917, compound → HCID 67231047, compound

HRID 1511913Notes

Reaction equation

HRID 1511913 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([N:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)C(OC(C)(C)C)=O)[C:7]([Cl:12])=[C:8]([Cl:11])[C:9]=1[Cl:10])=[O:4]>ClCCl.C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:13][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:7]([Cl:12])=[C:8]([Cl:11])[C:9]=1[Cl:10])=[O:4]

Participants

4

Reactant 1

HCID 68760917HCID 68760917, compound

Product 1

HCID 67231047HCID 67231047, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1-(Benzyl-tert-butoxycarbonyl-amino)-3,4,5-trichloro-1H-pyrrole-2-carboxylic acid methyl ester (509 mg, 1.17 mmol) was stirred in a mixture of dichloromethane (5 mL) and TFA (5 mL) at rt for 30 m in; then concentrated, the residue was dissolved in EtOAc, washed with diluted sodium bicarbonate, and saturated NaCl solution, dried over sodium sulfate, filtered, concentrated to give the crude product (394 mg) as white solid. ESI (m/z): 334 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with diluted sodium bicarbonate, and saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b7a3bc092cd438791990e9243ca881d
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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