Triethylamine → HCID 10203060, compound

HRID 1790649Notes

Reaction equation

HRID 1790649 reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:24][C:25]([C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)=[O:26])[C:9](=[O:23])[NH:10][C@H:11]2[CH2:17][CH2:16][C@@H:15]([CH3:18])[N:14]([CH2:19][CH2:20][CH3:21])[CH2:13][C@@H:12]2[OH:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C>CS(C)=O.O>[CH:1]1([CH2:7][C@H:8]([NH:24][C:25]([C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)=[O:26])[C:9](=[O:23])[NH:10][C@H:11]2[CH2:17][CH2:16][C@@H:15]([CH3:18])[N:14]([CH2:19][CH2:20][CH3:21])[CH2:13][C:12]2=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86588453HCID 86588453, compound

Product 1

HCID 10203060HCID 10203060, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sulfur trioxide-pyridine complex (0.0.35 g, 2.2 mmol) was added to a solution of Furan-2-carboxylic acid [(S)-2-cyclohexyl-1-((3S,4S,7R)-3-hydroxy-7-methyl-1-propyl-azepan-4-ylcarbamoyl)-ethyl]-amide (0.19 g, 0.44 mmol) in DMSO (4.0 ml) and triethylamine (0.61 ml, 4.4 mmol) was stirred at RT for 1 h. The reaction mixture was diluted with water, then was extracted with EtOAc. Then, the organic layer was was extracted with brine. The combined organics were dried with magnesium sulfate, filtered, concentrated in vacuo, and purified by column chromatography (3% methanol/methylene chloride) gave the title compound (0.15 mg, 79%): 1H NMR: 7.44(s, 1 H), 7.11(d, 1 H), 7.04(d, 1 H), 6.92(d, 1 H), 6.49(d, 1 H), 5.29(m, 1 H), 4.69(m, 1 H), 3.40(d, 1 H), 3.08(m, 2 H), 2.51(m, 2 H), 1.88–0.81(m, 29 H); Electrospray mass spec: M+H+=432.2.

Workup

  1. extractionwas extracted with EtOAc
  2. extractionThen, the organic layer was was extracted with brine
  3. dry with materialThe combined organics were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (3% methanol/methylene chloride)

Sources & evidence

ORD record
ord-808d165d121346eab84240fc7724fb06
Source dataset
uspto-grants-2006_07
Patent number
US07071184B2

Reaction notes

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