Benzoyl chloride → HCID 131725181, compound

HRID 966538Notes

Reaction equation

HRID 966538 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH3:17])=[C:11]2[C:18]([OH:20])=[O:19])(=O)=O.C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C.[C:28]([Cl:36])(=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH2:37]1COCC1>>[ClH:36].[C:29]1([C@@H:28]([O:20][C:18]([C:11]2[C:10]3[C:14](=[CH:15][CH:16]=[C:8]([CH2:7][CH2:6][N:23]([CH2:24][CH3:25])[CH2:26][CH3:27])[CH:9]=3)[NH:13][C:12]=2[CH3:17])=[O:19])[CH3:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 7412Benzoyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 22311862HCID 22311862, compound

Product 1

HCID 131725181HCID 131725181, compoundYield 81%

Procedure

To a mixture of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-caboxylic acid (285 mg, 0.96 mmol) and triethylamine (0.134 mL, 0.96 mmol) in dry THF (10 mL) was added benzoyl chloride (0.11 mL, 0.96 mmol). The mixture was stirred under nitrogen atmosphere at room temperature for 3 hours. The mixture was filtered and the filtrate was concentrated in vacuo to give a residue, which was triturated with diethyl ether to give 310 mg (81%) of the desired product as a off-white foam: MS(APCI−): m/z 400.0 (M−H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a residue, which
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-f7d8629c070a4a8389a281073759016d
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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