Triethylamine → HCID 86756990, compound

HRID 1796866Notes

Reaction equation

HRID 1796866 reaction equation
[NH2:1][C@H:2]([CH2:8][CH2:9][S:10][CH3:11])[CH:3]([OH:7])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[C:19]([O:23][C:24](ON=C(C1C=CC=CC=1)C#N)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCOCC1>[C:19]([O:23][C:24]([NH:1][C@H:2]([CH2:8][CH2:9][S:10][CH3:11])[CH:3]([OH:7])[C:4]([OH:6])=[O:5])=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 10219671HCID 10219671, compound

Product 1

HCID 86756990HCID 86756990, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 1C (2.68 g, 12.5 mmol), triethylamine (3.47 ml, 75.0 mmol), and 2-(tert-butyoxycarbonyloxyimino)-2-phenylacetonitrile (3.22 g, 13.0 mmol) in 30% aqueous dioxane was heated to 50° C. for 6 hours, cooled to ambient temperature, and concentrated. The residue was diluted with aqueous sodium hydroxide (0.25M, 50 mL) and extracted twice with ethyl acetate. The aqueous layer was acidified to pH 3 with 1M H3PO4 and extracted five times with chloroform. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide the desired product (1.62 g). MS (ESI) m/e 278 (M−H)−.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with aqueous sodium hydroxide (0.25M, 50 mL)
  3. extractionextracted twice with ethyl acetate
  4. extractionextracted five times with chloroform
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-edc47b4aa4dc4bc49395d706e44a2e60
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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