Trityl chloride → HCID 69748114, compound

HRID 1530864Notes

Reaction equation

HRID 1530864 reaction equation
[OH:1][CH:2]([CH2:24][OH:25])[CH2:3][NH:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:26]1([C:32](Cl)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl.N1C=CC=CC=1>[OH:1][CH:2]([CH2:24][O:25][C:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[CH2:3][NH:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 53324037HCID 53324037, compound

Product 1

HCID 69748114HCID 69748114, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

A solution of 9 (28 mmol) in 80 ml of dichloromethane/pyridine (1:1) is added dropwise with triphenylmethyl chloride (36 mmol) and stirred at room temperature for 48 hours. The solvent is removed, and the residue is added twice with 50 ml of toluene and concentrated. The residue is diluted with 100 ml of H2O and extracted three times with 50 ml of dichloromethane. The combined organic phases are washed with 50 ml of cold 5% HCl and 50 ml of saturated NaCl solution, dried over MgSO4, filtrated and concentrated. The residue is purified by chromatography on silica gel using heptane/ethyl acetate (2:1). Yield: 81% of a colorless oil.

Workup

  1. customThe solvent is removed
  2. additionthe residue is added twice with 50 ml of toluene
  3. concentrationconcentrated
  4. additionThe residue is diluted with 100 ml of H2O
  5. extractionextracted three times with 50 ml of dichloromethane
  6. washThe combined organic phases are washed with 50 ml of cold 5% HCl and 50 ml of saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltrated
  9. concentrationconcentrated
  10. customThe residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c2fcc23b139e448c872703e945082f2c
Source dataset
uspto-grants-2001_03
Patent number
US06197759B1

Reaction notes

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