Water → HCID 66614597, compound

HRID 77502Notes

Reaction equation

HRID 77502 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].O.[CH2:6]([O:8][C:9](=[O:54])[C:10]([CH3:53])([CH3:52])[CH2:11][C:12]1[N:13]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]3[CH:45]=[N:46][C:47]([O:50][CH3:51])=[CH:48][CH:49]=3)=[CH:40][CH:39]=2)[C:14]2[C:19]([C:20]=1SC(C)(C)C)=[CH:18][C:17]([O:26][CH2:27][C:28]1[S:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=1)=[CH:16][CH:15]=2)[CH3:7]>C(Cl)Cl>[CH2:6]([O:8][C:9](=[O:54])[C:10]([CH3:53])([CH3:52])[CH2:11][C:12]1[N:13]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]3[CH:45]=[N:46][C:47]([O:50][CH3:51])=[CH:48][CH:49]=3)=[CH:40][CH:39]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:26][CH2:27][C:28]1[S:29][C:30]3[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=3[N:32]=1)=[CH:16][CH:15]=2)[CH3:7]

Participants

5

Reactant 3

HCID 962Water2×HCID 6451240Aluminum(III) ChlorideHCID 666123743-{5-(Benzothiazol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid ethyl ester

Product 1

HCID 66614597HCID 66614597, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Aluminum chloride (0.18 g, 1.37 mmol) was suspended in CH2Cl2 (1 mL), and water (19 uL, 1.0 mmol) was added slowly at room temperature. The mixture was stirred for 5 minutes, and then cooled to 0° C. 3-{5-(Benzothiazol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid ethyl ester (0.12 g, 0.17 mmol) was added in CH2Cl2 (1 mL), and the reaction was stirred at room temperature for 2 hours. Once no starting material was observed by tlc, water was added and the mixture was extracted with CH2Cl2. The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated. The residue was purified to give the desired product (H-1).

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. additionwas added
  3. extractionthe mixture was extracted with CH2Cl2
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-38a81f0a1a5545e49702306203c624e0
Source dataset
uspto-grants-2014_09
Patent number
US08841295B2

Reaction notes

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