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Thioglycolic Acid → Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)propanoate

HRID 1049425
Notes
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Reaction equation

HRID 1049425 reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][N:18]([C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=4[F:45])=[C:33]([CH2:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH:32]=3)S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.SCC(O)=O.O.[OH-].[Li+].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][NH:18][C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=4[F:45])=[C:33]([CH2:46][C:47]([CH3:48])([CH3:50])[CH3:49])[CH:32]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1133Thioglycolic AcidHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 117759657ethyl 3-cyclopropyl-3-(3-((N-(2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)-2-nitrophenylsulfonamido)methyl)phenyl)propanoate

Product 1

HCID 117759818
Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)propanoate
Yield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-cyclopropyl-3-(3-((N-(2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)-2-nitrophenylsulfonamido)methyl)phenyl)propanoate (1.22 g) in DMF (35 mL) were added mercaptoacetic acid (617 μL) and lithium hydroxide monohydrate (728 mg) at room temperature, and the mixture was stirred at 60° C. for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (801 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-197b1f5e0a754cc38157e8ce2e4f2f4b
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09382188B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes