Trifluoroacetic acid → HCID 68671068, compound

HRID 1526019Notes

Reaction equation

HRID 1526019 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([O:15][CH2:16][C@@H:17]2[CH2:21][CH2:20][CH2:19][N:18]2[CH3:22])[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[O:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:22][N:18]1[CH2:19][CH2:20][CH2:21][C@H:17]1[CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:3]([C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5])=[C:2]([NH:1][CH:26]2[CH2:27][CH2:28][O:23][CH2:24][CH2:25]2)[CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 68671314HCID 68671314, compound

Product 1

HCID 68671068HCID 68671068, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 2-amino-4-{[(2S)-1-methylpyrrolidin-2-yl]methoxy}benzoate (400 mg, 1.3 mmol) was dissolved in 20 ml of DCM under argon atmosphere. Tetrahydro-4H-pyran-4-one (0.19 ml, 2.05 mmol), TFA (0.29 ml, 3.69 mmol) and Me4BH(OAc)3, (540 mg, 2.05 mmol) were added. The resulting slurry was stirred overnight at room temperature then quenched with 15 ml of NaHCO3 10% and extracted twice with 20 ml of DCM. The organic layers were then dried over Na2SO4, filtered off and concentrated to yield a yellow oil (448 mg, 1.15 mmol, 88%) which was used in the next step without any further purification.

Workup

  1. customthen quenched with 15 ml of NaHCO3 10%
  2. extractionextracted twice with 20 ml of DCM
  3. dry with materialThe organic layers were then dried over Na2SO4
  4. filtrationfiltered off
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dad3feeece1f4dd982c783a9c4e9edf8
Source dataset
uspto-grants-2015_07
Patent number
US09085558B2

Reaction notes

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