Hydrochloric Acid → HCID 59334893, compound

HRID 1517968Notes

Reaction equation

HRID 1517968 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]([S:27]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1)(=[O:29])=[O:28])[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19](=[O:22])[NH:20][CH3:21])[CH2:14][CH:13]2[C:23]([O:25]C)=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl.[Cl-].[Na+]>O1CCCC1.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([CH2:8][N:9]([S:27]([C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[CH:31]=1)(=[O:28])=[O:29])[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19](=[O:22])[NH:20][CH3:21])[CH2:14][CH:13]2[C:23]([OH:25])=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 5234Sodium ChlorideHCID 59334862HCID 59334862, compound

Product 1

HCID 59334893HCID 59334893, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 mg methyl 5-[tert-butoxycarbonylmethyl-(3,5-dichloro-phenylsulphonyl)-amino]-1-methylcarbamoyl-2,3-dihydro-1H-indole-3-carboxylate are dissolved in 1.2 ml of tetrahydrofuran, combined with 349 μl of a 1 M solution of lithium hydroxide in water and stirred overnight at ambient temperature. Then the mixture is cooled to 0° C., combined with 350 μl 1 M hydrochloric acid and divided between ethyl acetate and saturated sodium chloride solution. The organic phase is dried on magnesium sulphate and the solvents are eliminated in vacuo. The residue is chromatographed on silica gel (dichloromethane/methanol 20:1).

Workup

  1. temperatureThen the mixture is cooled to 0° C.
  2. customThe organic phase is dried on magnesium sulphate
  3. customThe residue is chromatographed on silica gel (dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-9b60bce00af24c9c882a089b5297efce
Source dataset
uspto-grants-2012_07
Patent number
US08232312B2

Reaction notes

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