Water → HCID 68715097, compound

HRID 1159802Notes

Reaction equation

HRID 1159802 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[C:18]([C:35]([O:37]CC)=[O:36])[N:19]3[S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+:41].O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[C:18]([C:35]([O-:37])=[O:36])[N:19]3[S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:27])=[O:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[Li+:41]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68717065HCID 68717065, compound2×

Product 1

HCID 68715097HCID 68715097, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 4-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}-5-methoxy-1-(phenylsulfonyl)-1H-indole-2-carboxylate (330 mg, 0.6 mmol, Intermediate 56) was dissolved in THF (10 mL) before lithium hydroxide (17 mg, 0.7 mmol) was added followed by 4 mL water. The reaction mixture was heated to 70° C. for 24 h before the reaction was completed. The reaction mixture was evaporated. This gave 3 g of a white solid which was washed with several portions of hot DCM and then hot THF. The combined wash phases were evaporated. This gave 270 mg of a slightly brown solid. Yield 83%. MS (ESI+) for C26H30N3O7SLi m/z 530 (M+H)+.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated
  3. washThis gave 3 g of a white solid which was washed with several portions of hot DCM
  4. washThe combined wash phases
  5. customwere evaporated

Sources & evidence

ORD record
ord-b5d8c0c46af84005b3e8f698b853e1f6
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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