Hydrochloric Acid → HCID 9811096, compound

HRID 1936902Notes

Reaction equation

HRID 1936902 reaction equation
[C:1](=[O:4])([O-:3])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:55])[C@H:10]([O:24][C:25]1[C:30]([Br:31])=[CH:29][C:28]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[C:39]4[CH:53]=[CH:52][CH:51]=[CH:50][C:40]=4[S:41][C:42]=3[CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:34][CH:33]=2)=[CH:27][C:26]=1[Br:54])[CH2:11][CH2:12][N:13]1C(=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].CO.Cl>O>[CH2:43]([C:42]1[S:41][C:40]2[CH:50]=[CH:51][CH:52]=[CH:53][C:39]=2[C:38]=1[C:35]1[CH:36]=[CH:37][C:32]([C:28]2[CH:27]=[C:26]([Br:54])[C:25]([O:24][C@@H:10]([C:9]([O:8][CH3:7])=[O:55])[CH2:11][CH2:12][NH:13][C:14](=[O:23])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:1]([OH:3])=[O:4])=[C:30]([Br:31])[CH:29]=2)=[CH:33][CH:34]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 54440153HCID 54440153, compound

Product 1

HCID 9811096HCID 9811096, compoundYield 624.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Potassium carbonate (0.01 g) was added into a mixture of (2R)-2-[4′-(2-benzyl-benzo[b]-thiophen-3-yl)-3,5-dibromo-biphenyl-4-yloxy]-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid methyl ester (0.5, 0.063 mmol), methyl alcohol (10 mL), and water (0.5 mL). The reaction mixture was stirred at room temperature for 24 hours, poured into water, acidified with HCl (2 N), and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on acidic silica gel (hexanes/EtAOc 4:1) gave white solid (0.32 g, 63% yield): mp 95-97° C; MS m/e 811 (M+);

Workup

  1. extractionextracted with ethyl ether
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography on acidic silica gel (hexanes/EtAOc 4:1)

Sources & evidence

ORD record
ord-e10c291f5e5047b79db7eb1fa5629633
Source dataset
uspto-grants-2002_05
Patent number
US06391897B2

Reaction notes

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