Triethylamine → HCID 86600894, compound

HRID 2110332Notes

Reaction equation

HRID 2110332 reaction equation
[OH:1][CH:2]([CH:16]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[N:23]1([CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:2]([O:1][S:40]([CH3:39])(=[O:42])=[O:41])[CH2:3][O:4][C:5](=[O:15])[C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68906871HCID 68906871, compound

Product 1

HCID 86600894HCID 86600894, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2RS, 3RS)-4-nitro-benzoic acid 2-hydroxy-3-indol-1-yl-3-phenyl-propyl ester and triethylamine (1.4 mL, 10.5 mmol) in dichloromethane (20 mL) was added methanesulfonyl chloride (0.59 mL, 7.6 mmol) dropwise at 0-5° C. with stirring. After stirring for 30 minutes, the mixture was washed with a 1N aqueous solution of hydrochloric acid, 5% aqueous sodium bicarbonate, and water, dried over anhydrous sodium sulfate, filtered, and concentrated to give a light yellow fluffy solid. The crude product was recrystallized from dichloromethane with a minimum amount of diethyl ether to give (2RS,3RS)-4-nitro-benzoic acid-3-indol-1-yl-2-methanesulfonyloxy-3-phenyl-propyl ester as a yellow solid. MS (ESI) m/z 495 ([M+H]+).

Workup

  1. stirringAfter stirring for 30 minutes
  2. washthe mixture was washed with a 1N aqueous solution of hydrochloric acid, 5% aqueous sodium bicarbonate, and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a light yellow fluffy solid
  7. customThe crude product was recrystallized from dichloromethane with a minimum amount of diethyl ether

Sources & evidence

ORD record
ord-edf27ac64110401daa26840aa4b812a3
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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