Sodium Hydroxide → HCID 59616761, compound

HRID 2364830Notes

Reaction equation

HRID 2364830 reaction equation
C([O:3][C:4]([C@@H:6]1[CH:11]2[CH2:12][CH:8]([CH2:9][CH2:10]2)[NH:7]1)=[O:5])C.[CH3:13][O:14][C:15]([NH:17][C@@H:18]([CH:22]([CH3:24])[CH3:23])[C:19](O)=[O:20])=[O:16].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>CN(C)C=O.O.C(O)C>[CH3:13][O:14][C:15]([NH:17][C@@H:18]([CH:22]([CH3:24])[CH3:23])[C:19]([N:7]1[C@H:6]([C:4]([OH:3])=[O:5])[CH:11]2[CH2:12][CH:8]1[CH2:9][CH2:10]2)=[O:20])=[O:16]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 60010725HCID 60010725, compound

Product 1

HCID 59616761HCID 59616761, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

(3S)-ethyl2-azabicyclo[2.2.1]heptane-3-carboxylate (1.25 g, 7.39 mmol), (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (1.42 g, 8.13 mmol), diisopropylethylamine (6.45 mL, 36.9 mmol), and HATU (2.95 g, 7.76 mmol) were combined in dimethylformamide (40 mL) at ambient temperature and stirred for 2 hours. The solution was diluted with water and the product filtered and dried. The dried ester (1.0 g, 3.06 mmol) was taken up in water (15 mL) and ethanol (15 mL) and treated with sodium hydroxide (0.5 g, 12.5 mmol) at ambient temperature for 17 hours. The solution was washed with ether then the aqueous was neutralized with concentrated HCl to pH 7 and the product extracted into ethyl acetate, dried over sodium sulfate, and concentrated to give the title compound as a waxy solid.

Workup

  1. filtrationthe product filtered
  2. customdried
  3. washThe solution was washed with ether
  4. extractionthe product extracted into ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-89c83e9114ad43bd9c6021c4dd7f6d0b
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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