Tetrahydrofuran → HCID 68716901, compound

HRID 1159799Notes

Reaction equation

HRID 1159799 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([CH2:19][N:20]4[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:22]([C:33]([O:35]C)=[O:34])[CH2:21]4)[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1>[OH-].[K+].CO>[C:29]([O:28][C:26]([N:23]1[CH2:24][CH2:25][N:20]([CH2:19][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[CH:12]=[CH:11][N:10]3[S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])[CH2:21][CH:22]1[C:33]([OH:35])=[O:34])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68718016HCID 68718016, compound

Product 1

HCID 68716901HCID 68716901, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

1-tert-Butyl 2-methyl 4-{[1-(phenylsulfonyl)-1H-indol-4-yl]methyl}piperazine-1,2-dicarboxylate (all of Intermediate 50) was dissolved in 1M KOH (3 mL) in MeOH (3 mL) and THF (3 mL) and stirred overnight. The mixture was evaporated and diluted with dichloromethane and water. pH was adjusted to 4 with 1N HCl (2.5 mL) and saturated solution of dihydrogenphosphate. The organic phase was evaporated and purified by flash chromatography using 2.5% MeOH to 5% MeOH in dichloromethane. Yield: 85 mg (30%, calculated from 1-(phenylsulfonyl)-1H-indole-4-carbaldehyde). White solid. MS (electronspray; [M+H]+) m/z 500.4.

Workup

  1. customThe mixture was evaporated
  2. additiondiluted with dichloromethane and water
  3. customThe organic phase was evaporated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c612fe00091c417894f87c15436bc1f6
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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