Potassium Carbonate → Fmoc-Hyp(OEt)-OH

HRID 1482232Notes

Reaction equation

HRID 1482232 reaction equation
C([NH:3][C@@H:4]([CH2:8][C:9]1[CH:14]=CC=CC=1)[C:5]([OH:7])=[O:6])C.[C:15](=[O:18])([O-:17])[O-].[K+].[K+].C(=O)(ON1C(=O)CCC1=O)O[CH2:23][CH:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2.S(=O)(=O)(O)[O-].[K+].[O:52]1CCO[CH2:54][CH2:53]1>O>[CH:29]1[C:30]2[CH:35]([CH2:34][O:17][C:15]([N:3]3[CH2:14][C@H:9]([O:52][CH2:53][CH3:54])[CH2:8][C@H:4]3[C:5]([OH:7])=[O:6])=[O:18])[C:36]3[C:24](=[CH:23][CH:33]=[CH:32][CH:31]=3)[C:25]=2[CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 312751,4-Dioxane2×HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516920Potassium bisulfateHCID 1056663983545-04-4

Product 1

HCID 89668655Fmoc-Hyp(OEt)-OHYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-2-(Ethylamino)-3-phenylpropanoic acid (Compound SP442) (4.00 g, 20.7 mmol) was dissolved in a mixture of 1,4-dioxane (100 ml) and water (100 ml), potassium carbonate (8.69 g, 62.9 mmol) and (9H-fluoren-9-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate (6.98 g, 20.7 mol) were added, and the mixture was stirred at room temperature for 8 hours. The aqueous layer was adjusted to pH 4 with a aqueous potassium bisulfate solution, and 1,4-dioxane was evaporated under reduced pressure. The resulting aqueous solution was extracted with ethyl acetate, and the resulting organic extract was washed with brine, dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate:petroleum ether=1:1) to afford (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-ethoxypyrrolidine-2-carboxylic acid (Compound SP443) (3.2 g, 37%).

Workup

  1. additionwere added
  2. customwas evaporated under reduced pressure
  3. extractionThe resulting aqueous solution was extracted with ethyl acetate
  4. extractionthe resulting organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography (ethyl acetate:petroleum ether=1:1)

Sources & evidence

ORD record
ord-0ac5177e45b04cb3be332a56336c949c
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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