Acetic Acid → HCID 67235543, compound

HRID 1748314Notes

Reaction equation

HRID 1748314 reaction equation
[NH2:1][C:2]([CH3:21])([CH3:20])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[CH:7]=[C:6]1[C:17](O)=[O:18].C(N1C=CN=C1)(N1C=CN=C1)=O.N12CCCN=C1CCCCC2.C(O)(=O)C>C1COCC1.O>[CH3:20][C:2]1([CH3:21])[CH2:3][CH2:4][N:5]2[C:13]3[CH:12]=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=[CH:9][C:8]=3[CH:7]=[C:6]2[C:17](=[O:18])[NH:1]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67236248HCID 67236248, compound

Product 1

HCID 67235543HCID 67235543, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude 1-(3-Amino-3-methylbutyl)-1H-indole-2,6-dicarboxylic acid from the preceding step in THF (9.0 mL) is added 1,1′-carbonyldiimidazole (162 mg, 0.90 mmol) followed by 1,8-diazabicyclo[5.4.0] undec-7-ene (0.14 mL, 0.90 mmol). The mixture is stirred at room temperature for 2 h. Acetic acid (0.3 mL) and water (50 mL) are added and the mixture is extracted with EtOAc. The organic layers are dried (Na2SO4) and concentrated. The crude compound is purified by flash column chromatography using 10% methanol in CH2Cl2 to afford the title compound (17 mg, 16% for three steps).

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialThe organic layers are dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude compound is purified by flash column chromatography

Sources & evidence

ORD record
ord-40aed164b44848e89c1c5bfeaf33580b
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

Loading…