Cyclooctanone → HCID 20794995, compound

HRID 1070566

Reaction equation

HRID 1070566 reaction equation
[C:1]([CH:5]([C:12]([OH:14])=[O:13])[CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:15]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C)C=O.C(O)(=O)C>[CH:15]1([NH:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:12]([OH:14])=[O:13])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 10403CyclooctanoneHCID 5049666Sodium triacetoxyborohydrideHCID 18611299HCID 18611299, compound

Product 1

HCID 20794995HCID 20794995, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21926011acetic acid N,N-dimethylformamideSolvent

Procedure

To a stirred suspension of γ-tert-butyl-L-glutamic acid (4.06 g, 20.0 mmol) and cyclooctanone (3.15 g, 25 mmol) in N,N-dimethylformamide/acetic acid (99:1, v/v, 50 mL) was added sodium triacetoxyborohydride (6.36 g, 30.0 mmol) in small portions and the mixture was stirred overnight. After evaporation of the solvent, the residue was dissolved in water (50 mL). The pH was adjusted to 9 with 2 N sodium hydroxide solution, followed by extraction with diethylether (50 mL). Subsequently, the pH of the aqueous layer was carefully adjusted to 2.5 using 1.0 N hydrochloric acid. Extraction with dichloromethane afforded an organic layer, which was dried (magnesium sulphate) and concentrated under reduced pressure, yielding 4.82 g (77%) of the title compound as a white solid. ESI-MS: 314.2 (M+H)+, 336.2 (M+Na)+. Rf (silica gel; ethyl acetate/pyridine/acetic acid/water 63:20:6:11, v/v): 0.80.

Workup

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue was dissolved in water (50 mL)
  3. extractionfollowed by extraction with diethylether (50 mL)
  4. extractionExtraction with dichloromethane
  5. customafforded an organic layer, which
  6. dry with materialwas dried (magnesium sulphate)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2a1594e01674934b1831cd8b4d0e173
Source dataset
uspto-grants-2005_06
Patent number
US06903107B1

Linked notes

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