Aniline → HCID 59253798, compound

HRID 252694Notes

Reaction equation

HRID 252694 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][CH2:11][S:12][C:13]([F:16])([F:15])[F:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1COCC1.N#N>[C:36]1([NH:35][C:17]([C@@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:10][CH2:11][S:12][C:13]([F:14])([F:15])[F:16])=[O:19])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 1633439HCID 1633439, compound

Product 1

HCID 59253798HCID 59253798, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 947NitrogenSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Boc-trifluoromethionine (200 mg, 0.659 mmol) was dissolved in 6.6 ml of dry THF in the presence of N2, and the temperature was adjusted to −78° C. Subsequently, N-methylmorpholine (0.09 ml, 0.794 mmol) was added thereto, and the mixture was stirred. Two minutes later, isobutyl chloroformate (0.10 ml, 0.794 mmol) was added thereto, and the mixture was stirred for 2 minutes. Finally, aniline (0.07 ml, 0.794 mmol) was added thereto. TLC was performed to confirm disappearance of the starting compound, and the solid matters were filtered, followed by distillation of THF under reduced pressure. The residue was purified by column chromatography (hexane/ethyl acetate=80/20 then 70/30), thereby the product (168.6 mg, 65%) was obtained.

Workup

  1. customwas adjusted to −78° C
  2. stirringthe mixture was stirred for 2 minutes
  3. filtrationthe solid matters were filtered
  4. distillationfollowed by distillation of THF under reduced pressure
  5. customThe residue was purified by column chromatography (hexane/ethyl acetate=80/20

Sources & evidence

ORD record
ord-a4aabcb7f6d241839ca7ad15c5979149
Source dataset
uspto-grants-2011_01
Patent number
US07868206B2

Reaction notes

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