Methanol → HCID 68485877, compound

HRID 1875029Notes

Reaction equation

HRID 1875029 reaction equation
[OH-].[Li+].[CH3:3][C:4]([O:7][CH2:8][CH2:9][C:10]([NH:12][C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[C:18]([C:31]([O-:33])=[O:32])[N:19]2[C:22]([O:24]CCC(C)(C)C)=[O:23])=[CH:15][CH:14]=1)=[O:11])([CH3:6])[CH3:5].CO.O>C1COCC1>[CH3:3][C:4]([O:24][C:22]([N:19]1[C:20]2[C:16](=[CH:15][CH:14]=[C:13]([NH:12][C:10](=[O:11])[CH2:9][CH2:8][O:7][C:4]([CH3:3])([CH3:6])[CH3:5])[CH:21]=2)[CH:17]=[C:18]1[C:31]([OH:33])=[O:32])=[O:23])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 86761649HCID 86761649, compound

Product 1

HCID 68485877HCID 68485877, compoundYield 162.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium hydroxide (0.037 g, 1.55 mmol) was added to a solution of 1-(1,1-dimethylethyl)2-ethyl 6-({3-[(1,1-dimethylethyl)oxy]propanoyl}amino)-1H-indole-1,2-dicarboxylate (0.067 g, 0.155 mmol) in THF:methanol:water/3:1:1 (3 mL). The mixture was heated at 50° C. for 1 hr. The solvent was evaporated and the residue was dissolved in water, acidified with 1N aqueous HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to give the title compound (0.051 g, 108%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.40 (br. s., 1H), 9.82 (s, 1H), 7.94 (s, 1H), 7.44 (d, 1H), 7.04 (d, 1H), 6.85 (s, 1H), 3.57 (t, 2H), 2.33-2.48 (m, 2H), 1.09 (s, 9H). ES MS: m/z 305 (M+1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3fbc2c1abf394d569dba01f3f6b5bcc0
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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