Triethylamine → HCID 21971228, compound

HRID 1954085Notes

Reaction equation

HRID 1954085 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.C(N(CC)CC)C.[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20]>O.O1CCOCC1.CN(C)C1C=CN=CC=1>[CH2:17]([O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([N:5]2[CH2:6][C@H:2]([OH:1])[CH2:3][C@@H:4]2[C:7]([OH:9])=[O:8])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 440014Cis-4-Hydroxy-D-ProlineHCID 5179904-Butoxybenzenesulfonyl Chloride

Product 1

HCID 21971228HCID 21971228, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Cis-4-hydroxy-D-proline (0.308 g, 2.67 mmol) is dissolved in 16 mL of a 1:1 mixture of water and p-dioxane and then triethyl amine (0.819 mL, 5.89 mmol), 4-butoxyphenylsulfonyl chloride (0.700 g, 2.81 mmol), and 4-dimethylaminopyridine (0.033 g, 0.268 mmol) are added. The resulting solution is stirred at room temperature overnight. The reaction is then washed with sodium bicarbonate and extracted once with ether. The water layer is acidified with 1N HCl to pH=2 and extracted three times with ethyl acetate. The ethyl acetate layers are washed with ammonium chloride, dried (MgSO4), filtered and evaporated to give the crude compound. Cl+ MS: m/z (rel intensity) 361 (M+ +H, 40).

Workup

  1. washThe reaction is then washed with sodium bicarbonate
  2. extractionextracted once with ether
  3. extractionextracted three times with ethyl acetate
  4. washThe ethyl acetate layers are washed with ammonium chloride
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a5c0af005bce4472ae3b8d7d8c8a3577
Source dataset
uspto-grants-2000_09
Patent number
US06121272

Reaction notes

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