1-Butanol → HCID 22641890, compound

HRID 2415445Notes

Reaction equation

HRID 2415445 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[N:13]([C:19]([CH3:24])([CH3:23])[C:20](O)=[O:21])[CH2:12][CH2:11]3)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:34]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(O)CCC.[Cl-].[NH4+]>CN(C=O)C.O>[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[N:13]([C:19]([CH3:24])([CH3:23])[C:20]([NH2:34])=[O:21])[CH2:12][CH2:11]3)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 2631-ButanolHCID 25517Ammonium ChlorideHCID 2724699PyBOPHCID 22641887HCID 22641887, compound

Product 1

HCID 22641890HCID 22641890, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[6-(4-fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-2-methyl-propionic acid (175 mg, 0.490 mmol) and benzotriazol-1-yloxy-tripyrrolidino-phosphonium hexafluorophosphate (PyBOP, 382 mg, 0.735 mmol) and butanol (99.3 mg, 0.735 mmol) in N,N′-dimethylformamide (6 mL) was stirred at room temperature for 10 min. Ammonium chloride (52.4 mg, 0.979 mmol) was added and the mixture was stirred 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase is successively washed with sodium hydrogencarbonate 10% and MCI 0.1M. Drying and evaporation of the solvent left a solid which was recrystallised with ethyl acetate and ether (120 mg, 69%). MS: m/e=357.2-(M+H+).

Workup

  1. stirringthe mixture was stirred 2 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase is successively washed with sodium hydrogencarbonate 10% and MCI 0.1M
  4. customDrying
  5. customevaporation of the solvent
  6. waitleft a solid which
  7. customwas recrystallised with ethyl acetate and ether (120 mg, 69%)

Sources & evidence

ORD record
ord-ea26f5d661b3425eb239d905a1b149e6
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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