Potassium Carbonate → HCID 118260134, compound

HRID 1779194Notes

Reaction equation

HRID 1779194 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:23][C:24]#[C:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:23][C:24]#[C:25][CH3:26])=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 27568621-Bromo-2-butyneHCID 7019130Boc-Tyr-OMe

Product 1

HCID 118260134HCID 118260134, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, at room temperature, a commercially available reagent of methyl (S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionate (199 g, 673 mmol) was dissolved in DMF (795 mL), and a commercially available reagent of 1-bromo-2-butyne (100 g, 752 mmol) and potassium carbonate (112 g, 807 mmol) were added. The mixture was stirred at room temperature for 19 hours. To the reaction solution were added a saturated aqueous solution of ammonium chloride and ethyl acetate and the mixture was extracted. The organic layer was washed with water and a saturated brine in order, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off. The residue was then dried under reduced pressure to obtain methyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate (ESI (LC/MS positive mode) m/z 348 (M+H); Rt 2.50 min.; No. 4935047; 233 g, quant.).

Workup

  1. extractionthe mixture was extracted
  2. washThe organic layer was washed with water
  3. dry with materiala saturated brine in order, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationThe solvent was distilled off
  6. customThe residue was then dried under reduced pressure

Sources & evidence

ORD record
ord-662f1b3a4bfa46249eca4f2def8e98dc
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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