Hydrochloric Acid → HCID 67252403, compound

HRID 2427279Notes

Reaction equation

HRID 2427279 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:28][C:11]2[N:12]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:13]3[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][C:18]=3[C:10]=2[CH2:9]1)(C)(C)C.[ClH:30].[OH-].[Na+]>CCO>[ClH:30].[NH2:7][C@@H:8]1[CH2:28][C:11]2[N:12]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:13]3[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][C:18]=3[C:10]=2[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67251942HCID 67251942, compound

Product 1

HCID 67252403HCID 67252403, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
47.5 °C

Procedure

Equip a 3 L 3-necked round bottom flask with a heating mantle, air stirrer, temperature probe, nitrogen inlet, and addition funnel Charge the flask with (S)-(7-cyano-4-pyridin-2-ylmethyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-carbamic acid tert-butyl ester (85.0 g, 0.22 moles), and EtOH (850 mL). Add concentrated HCl (180 mL, 2.20 moles) in one portion. Heat the resulting solution to 45-50° C. and stir for 90 min, after which analyze by HPLC to indicate complete consumption of starting material. Transfer the mixture to a Buchi flask, dilute with deionized water (595 mL), and concentrate in vacuo to remove EtOH. Add EtOAc in two portions (2×170 mL) and re-strip to remove both the EtOAc and residual EtOH. Transfer the aqueous concentrate to a 5 L reaction flask, and cool to 10-15° C. While maintaining the temperature of the reaction at <30° C., adjust the pH of the solution to 11-12 by the drop-wise addition of 5 M NaOH (950 mL). Extract the resulting mixture with CH2Cl2 (1300 mL, 800 mL). Wash the combined CH2Cl2 extracts with deionized water (500 mL), dry over Na2SO4, and concentrate in vacuo to afford titled compound as a light green solid (65.0 g, 103%).

Workup

  1. customEquip a 3 L 3-necked round bottom flask
  2. additionwith a heating mantle, air stirrer, temperature probe, nitrogen inlet, and addition funnel
  3. customconsumption of starting material
  4. additionTransfer the mixture to a Buchi flask, dilute with deionized water (595 mL)
  5. concentrationconcentrate in vacuo
  6. customto remove EtOH
  7. customto remove both the EtOAc and residual EtOH
  8. concentrationaqueous concentrate to a 5 L reaction flask
  9. temperaturecool to 10-15° C
  10. temperatureWhile maintaining
  11. customthe temperature of the reaction at <30° C.
  12. extractionExtract the resulting mixture with CH2Cl2 (1300 mL, 800 mL)
  13. washWash the combined CH2Cl2
  14. dry with materialdry over Na2SO4
  15. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-c1b5d1797c454d56b52effe1aab77ba6
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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