Sodium Hydroxide → HCID 67339611, compound

HRID 1670115Notes

Reaction equation

HRID 1670115 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:13]([O:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([C:39]2[CH:43]=[CH:42][S:41][CH:40]=2)[CH:38]=1)C(O)=O)=[O:5])C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.C(O[C:82]([N:84]1[CH2:89][CH2:88][NH:87][CH2:86][CH2:85]1)=[O:83])(C)(C)C.[OH-].[Na+]>C(Cl)Cl.C(OCC)(=O)C.C(O)C.CN(C=O)C>[C:4]([CH2:6][CH2:7][C:8]1[C:9]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:38]=[C:37]([C:39]3[CH:43]=[CH:42][S:41][CH:40]=3)[CH:36]=[C:32]([C:82]([N:84]3[CH2:85][CH2:86][NH:87][CH2:88][CH2:89]3)=[O:83])[CH:31]=2)=[CH:10][CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])([OH:5])=[O:3]

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 2733179PyBroPHCID 67338878HCID 67338878, compound

Product 1

HCID 67339611HCID 67339611, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 3-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-5-thiophen-3-yl-benzoic acid (130 mg, 0.21 mmol), PyBroP (263 mg, 0.63 mmol) and diisopropylethylamine (0.11 mL, 0.63 mmol) in CH2Cl2 (4 mL)/DMF (1 mL) was added piperazine-1-carboxylic acid tert-butyl ester (63 mg, 0.63 mmol). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The total amount of the product obtained from the previous step was dissolved in ethanol (5 mL) and 1 M NaOH solution was added (2 mL) and the reaction mixture stirred for 3 h. Then the reaction mixture was diluted with ethyl acetate, washed with 10% aq. HCl and brine. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude oil was dissolved in 5 mL CH2Cl2 and 5 mL of TFA was added. The reaction mixture was stirred for 1 h and the solvents were evaporated. The crude oil was purified by preparative HPLC using acetonitrile/water gradient to afford the title compound.

Workup

  1. washwashed with brine
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe total amount of the product obtained from the previous step
  6. stirringthe reaction mixture stirred for 3 h
  7. washwashed with 10% aq. HCl and brine
  8. extractionThe organic extract
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. dissolutionThe crude oil was dissolved in 5 mL CH2Cl2
  12. addition5 mL of TFA was added
  13. stirringThe reaction mixture was stirred for 1 h
  14. customthe solvents were evaporated
  15. customThe crude oil was purified by preparative HPLC

Sources & evidence

ORD record
ord-0c9108b5690e47ea81a1bf44fe42e94a
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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