Diisopropylethylamine → Pbf-Ser-OMe

HRID 1617284Notes

Reaction equation

HRID 1617284 reaction equation
[NH2:1][C@H:2]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][OH:4].CCN(C(C)C)C(C)C.[S:18](Cl)([C:21]1[C:33]([CH3:34])=[C:32]2[C:26]([O:27][C:28]([CH2:31]2)([CH3:30])[CH3:29])=[C:24]([CH3:25])[C:22]=1[CH3:23])(=[O:20])=[O:19]>C(Cl)(Cl)Cl>[NH:1]([S:18]([C:21]1[C:33]([CH3:34])=[C:32]2[C:26]([O:27][C:28]([CH2:31]2)([CH3:30])[CH3:29])=[C:24]([CH3:25])[C:22]=1[CH3:23])(=[O:19])=[O:20])[C@H:2]([C:5]([O:7][CH3:8])=[O:6])[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723731(S)-methyl 2-amino-3-hydroxypropanoateHCID 41722792,3-Dihydro-2,2,4,6,7-pentamethyl-5-benzofuransulfonyl chloride

Product 1

HCID 131728312Pbf-Ser-OMeYield 82.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

H-Ser-OMe, 3.5 g (22.6 mmol), was suspended in (40 mL) of chloroform. Under ice cooling, DIEA (8.7 mL, 49.7 mmol) and Pbf-Cl (5.86 g, 20.3 mmol) were sequentially added and stirred overnight while gradually elevating to room temperature. After the reaction was stopped by adding satd. citric acid aqueous solution, chloroform was distilled off under reduced pressure and the whole was extracted with AcOEt. The organic layer was washed sequentially with satd. citric acid aqueous solution, satd. sodium bicarbonate aqueous solution and satd. sodium chloride aqueous solution, and then dried over anhydrous MgSO4. After concentration under reduced pressure, flash chromatography was performed using AcOEt: n-hexane=1:1 to give Pbf-Ser-OMe (6.94 g, 82.7%).

Workup

  1. customwhile gradually elevating to room temperature
  2. additionby adding satd
  3. distillationcitric acid aqueous solution, chloroform was distilled off under reduced pressure
  4. extractionthe whole was extracted with AcOEt
  5. washThe organic layer was washed sequentially with satd
  6. dry with materialsodium chloride aqueous solution, and then dried over anhydrous MgSO4
  7. concentrationAfter concentration under reduced pressure, flash chromatography

Sources & evidence

ORD record
ord-b4a7b10b60aa48eb9f5c093263aa8809
Source dataset
uspto-grants-2014_07
Patent number
US08765909B2

Reaction notes

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