Lithium hydroxide, monohydrate → HCID 59473680, compound

HRID 453877Notes

Reaction equation

HRID 453877 reaction equation
O[Li].O.[Cl:4][C:5]1[CH:6]=[CH:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[CH:18]=[CH:17]4)[C:10](=[O:31])[C:9]=12>O.CO>[Cl:4][C:5]1[CH:6]=[CH:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19]([CH2:23][C:24]([OH:26])=[O:25])[CH:18]=[CH:17]4)[C:10](=[O:31])[C:9]=12

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68499227HCID 68499227, compound

Product 1

HCID 59473680HCID 59473680, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of LiOH.H2O (4.0 equiv.) in water (5 ml) was added at 0° C. to a solution of tert-butyl 2-(5-(8-chloro-1-oxo-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1H-indol-1-yl)acetate (1.5 mmol, 1.0 equiv.) in MeOH (20 ml), and the mixture was heated for 16 h at 50° C. The methanol was concentrated under reduced pressure, and the aqueous residue was diluted with water (20 ml) and extracted with ethyl acetate (2×15 ml). The aqueous phase was adjusted to pH 4 with 1 M HCl, the desired product precipitating in the form of a white solid. The solid was filtered out and dried. Yield: 78%

Workup

  1. concentrationThe methanol was concentrated under reduced pressure
  2. additionthe aqueous residue was diluted with water (20 ml)
  3. extractionextracted with ethyl acetate (2×15 ml)
  4. customthe desired product precipitating in the form of a white solid
  5. filtrationThe solid was filtered out
  6. customdried

Sources & evidence

ORD record
ord-c4c5d148024c4e758ced79112a270224
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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