Hydrochloric Acid → HCID 70113314, compound

HRID 1977341Notes

Reaction equation

HRID 1977341 reaction equation
[OH-:1].[Na+].C[O:4][C:5](=[O:51])[C@H:6]([O:20][C:21]1[C:26]([Br:27])=[CH:25][C:24]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[C:35]4[CH:49]=[CH:48][CH:47]=[CH:46][C:36]=4[S:37][C:38]=3[CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:30][CH:29]=2)=[CH:23][C:22]=1[Br:50])[CH2:7][CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19].CO.Cl>O.O1CCCC1>[CH2:39]([C:38]1[S:37][C:36]2[CH:46]=[CH:47][CH:48]=[CH:49][C:35]=2[C:34]=1[C:31]1[CH:32]=[CH:33][C:28]([C:24]2[CH:23]=[C:22]([Br:50])[C:21]([O:20][C@@H:6]([C:5]([OH:4])=[O:51])[CH2:7][CH2:8][NH:9][C:10](=[O:19])[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]([OH:1])=[O:18])=[C:26]([Br:27])[CH:25]=2)=[CH:29][CH:30]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 54440153HCID 54440153, compound

Product 1

HCID 70113314HCID 70113314, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (2 N, 5.0 mL) 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 (1.0g, 1.26 mmol), methyl alcohol (10 ml) and tetrahydrofuran (10 mL). The reaction mixture was stirred at room temperature for 1 hour, 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 2:1) gave white solid (0.82 g, 74% yield): mp 130-132° C.; MS m/e 797 (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 2:1)

Sources & evidence

ORD record
ord-f977c2ab85734a789d2ce4e2cd601a2e
Source dataset
uspto-grants-2001_05
Patent number
US06232322B1

Reaction notes

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