Triethylamine → HCID 58808286, compound

HRID 900397Notes

Reaction equation

HRID 900397 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]([C:20]1[N:21]([CH3:29])[C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6].C(N(CC)CC)C>CS(C)=O>[CH:2]([C@@H:3]([NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[NH:17][C:18]([C:20]1[N:21]([CH3:29])[C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:10])[CH2:4][CH:5]([CH3:7])[CH3:6])=[O:1]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58808360HCID 58808360, compound

Product 1

HCID 58808286HCID 58808286, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Methyl-1H-indole-2-carboxylic acid [(1S,2R)-2-((S)-1-hydroxymethyl-3-methyl-butylcarbamoyl)-cyclohexyl]-amide (0.328 g, 0.82 mmol) was added to 6 mL of dry DMSO. Triethylamine (0.46 mL, 3.28 mmol) was added followed by sulfur trioxide pyridine complex (0.52 g, 3.28 mmol) and the mixture was stirred at room temperature for a half hour. The mixture was poured into 100 mL of ice water and extracted twice with ethyl acetate. The ethyl acetate extracts were rinsed twice with a 10% citric acid solution, twice with water and once with saturated aqueous sodium bicarbonate and dried over sodium sulfate. Concentration in vacuo gave 0.311 g (0.78 mmol) of 1-methyl-1H-indole-2-carboxylic acid [(1S,2R)-2-((S)-1-formyl-3-methyl-butylcarbamoyl)-cyclohexyl]-amide as a solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe ethyl acetate extracts were rinsed twice with a 10% citric acid solution, twice with water and once with saturated aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-649db5ac507e42e19c9d3181e89f8eb4
Source dataset
uspto-grants-2008_04
Patent number
US07358373B2

Reaction notes

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