Acetic Anhydride → HCID 178441344, compound

HRID 1086481Notes

Reaction equation

HRID 1086481 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@H:8]([CH2:10][NH:11][C:12]([CH3:24])([CH3:23])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[OH:9])=[CH:4][CH:3]=1.C(OC(=O)C)(=[O:27])C>N1C=CC=CC=1>[NH2:1][C:2]1[N+:7]([O-:27])=[CH:6][C:5]([C@H:8]([CH2:10][NH:11][C:12]([CH3:24])([CH3:23])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[OH:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15137725HCID 15137725, compound

Product 1

HCID 178441344HCID 178441344, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1.5 g of (R)-6-Amino-α-[[(1,1-dimethyl-2-(1H-indol-3-yl)ethyl)amino]methyl]-3-pyridinemethanol in 20 ml of pyridine under nitrogen, acetic anhydride (10 ml) is added and the reaction mixture stirred at ambient temperature overnight. The mixture is then concentrated under reduced pressure. The crude acetylated product is treated with 0.9 g of m-chloroperbenzoic acid in 20 ml of CH2Cl2 for 4 hours at room temperature. The reaction mixture is concentrated once again and redissolved in 10 ml of methanol and treated with excess methanolic KOH solution at room temperature for 6 hours. The mixture is partially concentrated and then diluted with water and extracted repeatedly with CH2Cl2. The combined extracts is backwashed with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. The solution is concentrated and the residue chromatographed on silica gel to give the (R)-6-Amino-α-[[(1,1-dimethyl-2-(1H-indol-3-yl)ethyl)amino]methyl]-3-pyridinemethanol-1-oxide.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. additionThe crude acetylated product is treated with 0.9 g of m-chloroperbenzoic acid in 20 ml of CH2Cl2 for 4 hours at room temperature
  3. concentrationThe reaction mixture is concentrated once again
  4. dissolutionredissolved in 10 ml of methanol
  5. additiontreated with excess methanolic KOH solution at room temperature for 6 hours
  6. concentrationThe mixture is partially concentrated
  7. additiondiluted with water
  8. extractionextracted repeatedly with CH2Cl2
  9. dry with materialdried with anhydrous magnesium sulfate
  10. concentrationThe solution is concentrated
  11. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-935f658227d945cf83ce4cddc6be6639
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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