Trifluoroacetic acid → HCID 59464032, compound

HRID 1713823Notes

Reaction equation

HRID 1713823 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[N:16]=[CH:15][C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>O>[O:4]=[C:5]1[CH2:10][CH2:9][CH:8]([C:11]2[N:16]=[CH:15][C:14]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59464264HCID 59464264, compound

Product 1

HCID 59464032HCID 59464032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice water cooled solution of benzyl [6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]carbamate, prepared as above, (4.94 g, 13.41 mmol) was added TFA (20 mL) followed by water (1.1 mL). The reaction mixture was allowed to stir at ambient temperature for 2 hours. It was treated with 2M NaOH to adjust the pH to 10 and then the mixture was extracted into EtOAc (3×200 mL), the organic phase was separated, dried (MgSO4) and concentrated to leave a gum, 4.05 g (12.26 mmol, 93%) which was used directly in the next stage; 1H NMR (CDCl3) δ 1.97-2.10 (m, 2H), 2.24-2.29 (m, 2H), 2.49-2.53 (m, 4H), 3.13-3.21 (m, 1H), 5.22 (s, 2H), 6.82 (s, 1H), 7.18 (d, 1H), 7.36-7.40 (m, 5H), 7.96 (s, 1H), 8.41 (s, 1H); MS m/e MH+ 325.

Workup

  1. extractionthe mixture was extracted into EtOAc (3×200 mL)
  2. customthe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto leave a gum, 4.05 g (12.26 mmol, 93%) which

Sources & evidence

ORD record
ord-308c03a546a541d4a2fc1c155f9b1e7c
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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