Dimethylamine → HCID 90060273, compound

HRID 1779253Notes

Reaction equation

HRID 1779253 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][NH:26][CH3:27].O1CCCC1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:10](=[O:11])[N:26]([CH3:27])[CH3:25])=[CH:15][CH:16]=1)[C:22]#[C:23][CH3:24]

Participants

8

Reactant 6

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 90060209HCID 90060209, compound

Product 1

HCID 90060273HCID 90060273, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-2-tert-Butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionic acid (432 mg, 1.29 mmol) was dissolved in DMF (5.0 mL), and a solution of dimethylamine in tetrahydrofuran (2.92 mL, 5.84 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (370 mg, 1.94 mmol), and 1-hydroxybenzotriazole (262 mg, 1.94 mmol) were added. The reaction mixture was stirred at room temperature for 72 hours, and then poured into an aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (103 mg, 22% yield).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aa8bc4accffa4379baf068555f87f6a6
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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