Triethylamine → HCID 13136842, compound

HRID 1156808Notes

Reaction equation

HRID 1156808 reaction equation
[C:1]1([S:7][C@@H:8]2[CH2:12][NH:11][C@H:10]([C:13]([OH:15])=[O:14])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:23]([O:27][C:28](ON=C(C1C=CC=CC=1)C#N)=[O:29])([CH3:26])([CH3:25])[CH3:24]>O.O1CCOCC1>[CH3:24][C:23]([CH3:26])([O:27][C:28]([N:11]1[CH2:12][C@@H:8]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9][C@H:10]1[C:13]([OH:15])=[O:14])=[O:29])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 11379084cis-4-phenylthio-l-prolin

Product 1

HCID 13136842HCID 13136842, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (cis)-4-(phenylthio)-L-proline (5 g) and triethylamine (3.4 g) in water (13 ml), a solution of 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile (6.0 g) in dioxane (13 ml) is added. The mixture is stirred at ambient temperature. After one hour, water (50 ml) is added, the mixture is washed with ethyl acetate and acidified to a pH of 3-4 with 10% citric acid. The oil that separates is extracted into ethyl acetate, washed with brine, and dried (MgSO4). The residue is dissolved in saturated sodium bicarbonate (50 ml) plus water (600 ml). The alkaline solution is washed with ether and acidified to a pH of 4 with 10% citric acid. The oil that separates from solution is extracted into ethyl acetate, washed with brine, and dried (MgSO4). The solvent is removed in vacuo to give the product as an oil (5.9 g) that gradually solidifies, melting point 110°-118° C.

Workup

  1. washthe mixture is washed with ethyl acetate
  2. extractionThe oil that separates is extracted into ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. dissolutionThe residue is dissolved in saturated sodium bicarbonate (50 ml)
  6. washThe alkaline solution is washed with ether
  7. extractionThe oil that separates from solution is extracted into ethyl acetate
  8. washwashed with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c12bac48ee024c1bbec17546041571f7
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

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