Water → HCID 86655530, compound

HRID 1746591Notes

Reaction equation

HRID 1746591 reaction equation
O.[CH3:2][N:3]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5]([CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])=[CH:4]1.C(=O)([O-])O.[Na+].[C:23]([C:25](=[CH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[F:43])[C:26](ON1C(=O)CCC1=O)=[O:27])#[N:24]>O1CCOCC1>[C:23]([C:25](=[CH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[F:43])[C:26]([NH:8][C@H:7]([C:9]([OH:11])=[O:10])[CH2:6][C:5]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]([CH3:2])[CH:4]=1)=[O:27])#[N:24]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 6761591-Methyl-L-tryptophanHCID 86655526HCID 86655526, compound

Product 1

HCID 86655530HCID 86655530, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To water (60 mL)-dioxane (60 mL) suspension of 1-methyl-L-tryptophan (2.1 g) was added sodium hydrogencarbonate (0.8 g) at 0° C., and the mixture was stirred for 30 minutes at room temperature. Dioxane (80 mL) solution of the compound obtained in Example 120 (2.6 g, 9.2 mmol) was added dropwise to the reaction mixture at 0° C., and the mixture was stirred for 21 hours at room temperature. The reaction mixture was concentrated to a ⅓ volume under a reduced pressure, water was added thereto, and the mixture was washed with diethyl ether. The aqueous layer was made acidic with a 10% aqueous citric acid solution, and thereafter extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, and thereafter dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under a reduced pressure was purified with silica gel chromatography (BW-127ZH, chloroform:methanol=50:1), to give the captioned compound (0.6 g, 17%) as an amorphous solid product.

Workup

  1. stirringthe mixture was stirred for 21 hours at room temperature
  2. concentrationThe reaction mixture was concentrated to a ⅓ volume under a reduced pressure, water
  3. additionwas added
  4. washthe mixture was washed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe residue obtained
  9. distillationby distilling off the solvent under a reduced pressure
  10. customwas purified with silica gel chromatography (BW-127ZH, chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-4dac6d929df44e45bbbe939005450b1f
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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