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Hydrochloric Acid → HCID 70113314, compound

HRID 1936903
Notes
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Reaction equation

HRID 1936903 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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 (1.0 g, 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-11ee60042bf844d382573eb0bd62d986
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06391897B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes