Hydrochloric Acid → 4'-(6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1'-biphenyl]-4-carboxylic acid

HRID 1050244Notes

Reaction equation

HRID 1050244 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]([O:35][C@H:36]3[CH2:45][O:44][C@H:43]4[C@@H:38]([O:39][CH:40]([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[O:41][CH2:42]4)[CH2:37]3)=[N:24][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.[OH-].[Na+].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]([O:35][C@H:36]3[CH2:45][O:44][C@H:43]4[C@@H:38]([O:39][CH:40]([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[O:41][CH2:42]4)[CH2:37]3)=[N:24][C:5]2=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131736056Methyl 4'-(6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 900448994'-(6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1'-biphenyl]-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of methyl 4′-(6-chloro-2-(((4aR,7R,8aS)-2-phenylhexahydropyrano-[3,2-d][1,3]dioxin-7-yl)oxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-5-yl)-[1,1′-biphenyl]-4-carboxylate (474 mg, 0.651 mmol) in THF (5.2 mL) under nitrogen was added a 2.5N aqueous solution of NaOH (5.2 mL, 10.4 mmol). The mixture was allowed to stir at 40° C. for 24 hours. The mixture was then cooled to room temperature and diluted with water (40 mL). The mixture was acidified with 1N aqueous HCl and extracted with EtOAc (2×70 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, and concentrated under reduced pressure to provide the title compound as a yellow solid. LC-MS: calculated for C38H40ClN3O7Si 713.23, observed m/e: 714.21 (M+H)+ (Rt 2.85/4 min).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. extractionextracted with EtOAc (2×70 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aa825dd842eb487aac1c1f69f9b61a93
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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