Sodium Chloride → HCID 58493943, compound

HRID 2360524Notes

Reaction equation

HRID 2360524 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[C:8]([O:44][CH3:45])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:43])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]([CH:32]3[CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33]3)=[O:31])[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[OH-].[Na+].[Cl-].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[C:8]([O:44][CH3:45])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:43])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][N:24]2[CH2:25][CH2:26][N:27]([C:30]([CH:32]3[CH2:35][NH:34][CH2:33]3)=[O:31])[CH2:28][CH2:29]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acid2×HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 58493976HCID 58493976, compound

Product 1

HCID 58493943HCID 58493943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

243 mg of tert-butyl 3-{4-[2-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenylcarbamoyl)-1-methyl-1H-indol-7-ylmethyl]-piperazine-1-carbonyl}-azetidine-1-carboxylate are dissolved in 3 ml dichloromethane, cooled to 0° C. and combined with 261 μl trifluoroacetic acid. The mixture is allowed to come up to ambient temperature and stirred for 12 hours. Then a further 1.5 ml of trifluoroacetic acid are added and the mixture is stirred for 2 hours. Then it is diluted with dichloromethane and adjusted to pH 9 with 1 N sodium hydroxide solution. Saturated sodium chloride solution and saturated potassium carbonate solution are added and the phases are separated. The aqueous phase is extracted twice with dichloromethane. The combined organic phases are dried on magnesium sulphate and the solvents are eliminated in vacuo.

Workup

  1. customto come up to ambient temperature
  2. stirringthe mixture is stirred for 2 hours
  3. customthe phases are separated
  4. extractionThe aqueous phase is extracted twice with dichloromethane
  5. customThe combined organic phases are dried on magnesium sulphate

Sources & evidence

ORD record
ord-dc38889abd6e495389c1c51f1f11ef9f
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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