Methanol → HCID 68480831, compound

HRID 1874950Notes

Reaction equation

HRID 1874950 reaction equation
CO.[CH3:3][S:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14](C(OCCC(C)(C)C)=O)[C:13]([C:27]([O-:29])=[O:28])=[CH:12]2.[Li+].[OH-]>C1COCC1>[CH3:3][S:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:27]([OH:29])=[O:28])=[CH:12]2

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86761648HCID 86761648, compound

Product 1

HCID 68480831HCID 68480831, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A methanol solution of 1-(1,1-dimethylethyl)2-ethyl 5-{[3-(methylthio)propyl]oxy}-1H-indole-1,2-dicarboxylate (0.488 g, 1.24 mmol) was treated with 1 N LiOH (4 mL). The reaction mixture turned cloudy, THF was added to redissolve the precipitate and the mixture was heated to 70° C. When no starting material remained as evident by TLC the reaction mixture was partitioned between EtOAc and water. The aqueous layer was separated and acidified with conc. HCl. The aqueous layer was extracted with EtOAc and the organic layer was evaporated to afford the title compound (0.263 g, 80%). 1H NMR (400 MHz, Acetone-d6) δ ppm 10.73 (br. s., 1H), 7.43 (d, 1H), 7.14 (d, 1H), 7.09-7.13 (m, 1H), 6.96 (dd, 1H), 4.09 (t, 2H), 2.68 (t, 2H), 2.08 (s, 3H), 2.04 (t, 2H). LCMS: m/z=264.1 (M−1).

Workup

  1. dissolutionto redissolve the precipitate
  2. customwas partitioned between EtOAc and water
  3. customThe aqueous layer was separated
  4. extractionThe aqueous layer was extracted with EtOAc
  5. customthe organic layer was evaporated

Sources & evidence

ORD record
ord-258dd3d3f3af4e578520b8d8a7cb68fc
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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