Triethylamine → 5-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966523Notes

Reaction equation

HRID 966523 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][OH:22])[CH:18]=2)[NH:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C1COCC1>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][O:22][S:32]([CH3:31])(=[O:34])=[O:33])[CH:18]=2)[NH:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 233938725-(2-Hydroxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 233938525-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl EsterYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-(2-hydroxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (1.02 g, 3.3 mmol) and triethylamine (0.92 mL, 6.6 mmol) in dry THF (10 mL) was added methanesulfonyl chloride (0.26 mL, 3.3 mmol) under nitrogen atmosphere at room temperature. The mixture was stirred at room temperature for 3 hours and then partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give 1.27 g (99%) of the desired product as a white solid: mp 122-124° C.; MS(APCI−): m/z 386.0 (M−H); Anal. Calcd for C20H21N1O5S1: C, 62.00; H, 5.46; N, 3.62; S, 8.28. Found: C, 61.95; H, 5.61; N, 3.54; S, 8.32.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f9ead18ba24842b58b451fbc19509a5d
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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