Sulfate Ion → HCID 69456184, compound

HRID 1351972Notes

Reaction equation

HRID 1351972 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([NH2:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:22][C@H:23]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[C:24](O)=[O:25].S([O-])([O-])(=O)=O.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>O1CCCC1.C(=O)([O-])O.[Na+].O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([NH:21][C:24](=[O:25])[C@H:23]([OH:22])[C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 6

HCID 1117Sulfate IonHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9925700HCID 9925700, compoundHCID 51668998HCID 51668998, compound

Product 1

HCID 69456184HCID 69456184, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (1R)-2-(7-(benzyloxy)-1H-indol-3-yl)-1-methyl-ethylamine (5.0 g, 17.8 mmol) in tetrahydrofuran (100 mL) are added successively with stirring (R)-2-hydroxy-2-(3-pyridyl)acetic acid.sulfate (4.68 g, 11.6 mmol), triethylamine (3.22 mL, 23.1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.hydrochloride (4.78 g, 24.9 mmol), and 1-hydroxybenzotriazole (3.36 g, 24.9 mmol) under ice-cooling, and the mixture is stirred at room temperature for 2.5 hours. The reaction mixture is diluted with a mixture of a saturated aqueous sodium hydrogen carbonate solution and water (1:1, 100 mL), and extracted with ethyl acetate (2×100 mL). The organic layers are combined and washed with a mixture of a saturated brine and water (1:1, 100 mL), dried over magnesium sulfate, and separated by filtration. The filtrate is concentrated under reduced pressure, and the obtained pale brown solid is dispersed into chloroform (80 mL). The insoluble white solid is collected by filtration, washed with chloroform (40 mL), and dried under reduced pressure to give the title compound (6.38 g, yield: 86%).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washwashed with a mixture of a saturated brine and water (1:1, 100 mL)
  3. dry with materialdried over magnesium sulfate
  4. customseparated by filtration
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. additionthe obtained pale brown solid is dispersed into chloroform (80 mL)
  7. filtrationThe insoluble white solid is collected by filtration
  8. washwashed with chloroform (40 mL)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-e8abf969243b41038e4f6121ca2d0e9e
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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