Ammonium Chloride → HCID 44545376, compound

HRID 2387336Notes

Reaction equation

HRID 2387336 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([S:38]([CH3:41])(=[O:40])=[O:39])=[CH:12][C:13]=1[C:14]#[C:15][CH2:16][C@@:17]([OH:37])([C:33]([F:36])([F:35])[F:34])[CH2:18][C:19]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[S:29]([CH3:32])(=[O:31])=[O:30])([CH3:21])[CH3:20])(C)(C)C.C1CCN2C(=NCCC2)CC1.[Cl-].[NH4+]>CO>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]([CH3:21])([CH3:20])[CH2:18][C@:17]([CH2:16][C:15]2[NH:7][C:8]3=[CH:9][N:10]=[C:11]([S:38]([CH3:41])(=[O:40])=[O:39])[CH:12]=[C:13]3[CH:14]=2)([OH:37])[C:33]([F:36])([F:35])[F:34])=[C:23]([S:29]([CH3:32])(=[O:30])=[O:31])[CH:24]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58026125HCID 58026125, compound

Product 1

HCID 44545376HCID 44545376, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of the {4-[(S)-6-(4-chloro-2-methanesulfonylphenyl)-4-hydroxy-6-methyl-4-trifluoromethylhept-1-ynyl]-6-methanesulfonylpyridin-3-yl}carbamic acid tert-butyl ester (18.3 g, 28.0 mmol) in 200 mL of methanol was added DBU (12.5 mL, 84.0 mmol). The reaction was heated to 70° C. for 1.5 hours. The reaction was added to a solution of saturated aqueous ammonium chloride solution resulting in the precipitation of a white solid that was collected by vacuum filtration. The solid was washed with water and, after drying under vacuum for 30 minutes, was suspended in 50 mL of cold diethyl ether then vacuum filtered again and washed with 50 mL of cold diethyl ether. The colorless solid was dried on the filter paper under suction to provide (R)-4-(4-chloro-2-methanesulfonylphenyl)-1,1,1-trifluoro-2-(5-methanesulfonyl-1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)-4-methylpentan-2-ol (15.4 g, 99%).

Workup

  1. customresulting in the precipitation of a white solid
  2. filtrationthat was collected by vacuum filtration
  3. washThe solid was washed with water
  4. customafter drying under vacuum for 30 minutes
  5. filtrationvacuum filtered again
  6. washwashed with 50 mL of cold diethyl ether
  7. customThe colorless solid was dried on the filter paper under suction

Sources & evidence

ORD record
ord-1118f5ee75b14fb28bd53856accc912b
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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