Triethylamine → HCID 10302436, compound

HRID 1790636Notes

Reaction equation

HRID 1790636 reaction equation
[OH:1][C@@H:2]1[C@@H:8]([NH:9][C:10]([C@@H:12]([NH:17][C:18]([C:20]2[O:28][C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)=[O:19])[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:7][CH2:6][C@@H:5]([CH3:29])[N:4]([S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)(=[O:32])=[O:31])[CH2:3]1.C(N(CC)CC)C>CS(C)=O.O>[CH3:15][CH:14]([CH3:16])[CH2:13][C@H:12]([NH:17][C:18]([C:20]1[O:28][C:27]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)=[O:19])[C:10](=[O:11])[NH:9][C@H:8]1[CH2:7][CH2:6][C@@H:5]([CH3:29])[N:4]([S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)(=[O:32])=[O:31])[CH2:3][C:2]1=[O:1]

Participants

5

Reactant 2

HCID 8471Triethylamine2×HCID 69913924HCID 69913924, compound

Product 1

HCID 10302436HCID 10302436, compoundYield 22.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Sulfur trioxide-pyridine complex (0.050 g, 0.31 mmol) was added to a solution of Furo[3,2-b]pyridine-2-carboxylic acid {(S)-1-[(3S,4S,7R)-3-hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-ylcarbamoyl]-3-methyl-butyl}-amide (0.056 g, 0.103 mmol) in DMSO (1.0 ml) and triethylamine (0.085 ml, 0.6 mmol) was stirred at RT for 1 h. The reaction was incomplete; therefore, additional triethyl amine (0.04 ml, 0.3 mmol) and sulfur trioxide-pyridine complex (0.0.025 g, 0.15 mmol) was added ant the reaction was stirred an additional hour. 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 (50% to 80% ethyl acetate/hexanes) gave the title compound (12.5 mg, 22%): 1H NMR: 1H NMR: 8.72 (1H, d), 8.66 (1H, d), 8.02 (1H, d), 7.93 (1H, dd), 7.85 (1H, d), 7.53 (1H, dd), 7.40 (1H, dd), 7.25 (d, 1H), 6.95 (1H, d), 5.15 (m, 1H), 4.77 (m, 2H), 3.72 (q, 1H), 2.20–2.08 (m, 2H), 1.78–1.50 (m, 5H), 1.22 (dd, 3H), 0.98 (m, 6H); Electrospray mass spec: M+H+=542.2.

Workup

  1. stirringwas stirred an additional hour
  2. extractionwas extracted with EtOAc
  3. extractionThen, the organic layer was was extracted with brine
  4. dry with materialThe combined organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (50% to 80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cb7ae3420b1542f3a6e98d11403f3c91
Source dataset
uspto-grants-2006_07
Patent number
US07071184B2

Reaction notes

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