Hydrochloric Acid → HCID 68284225, compound

HRID 1527170Notes

Reaction equation

HRID 1527170 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]([NH2:16])=[O:15])[CH:9]=[C:8]2[CH:17]=[O:18])[CH:2]=[CH2:3].CC(=CC)C.[O-:24]Cl=O.[Na+].Cl>C1COCC1.C(O)(C)(C)C.O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14](=[O:15])[NH2:16])[CH:9]=[C:8]2[C:17]([OH:24])=[O:18])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86673792HCID 86673792, compound

Product 1

HCID 68284225HCID 68284225, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

5-Allyloxy-3-formyl-indole-1-carboxylic acid amide (530 mg, 2.17 mmol) was dissolved in a mixture of THF (38 mL) and t-butanol (12 mL). 2-methyl-2-butene 2 M solution in THF (40 mL, 80 mmol) was added, followed by a water (9.5 mL) solution of NaClO2 (80%, 2.45 g, 21.7 mmol) and NaH2PO4 (2.08 g, 17.4 mmol). The resulting solution was stirred at RT for 1 h, until consumption of the starting material. HCl 1N (3 mL) was added, and the organic solvents were concentrated. The remaining aqueous layer was filtered and the resulting precipitate was washed with water and Et2O to give the desired compound. TLC, Rf (c-hexane/EtOAc 1:2)=0.08; LC/MS: 261.1 [M+H]+, 259.0 [M−H]−, 216.1 [M−CONH2]−, 519.1 [2M−H]−; tR (HPLC conditions a): 2.8 min.

Workup

  1. concentrationthe organic solvents were concentrated
  2. filtrationThe remaining aqueous layer was filtered
  3. washthe resulting precipitate was washed with water and Et2O

Sources & evidence

ORD record
ord-515412c497fa41d986e38d590449bbc2
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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