Hydrochloric Acid → Asp-4000

HRID 456778Notes

Reaction equation

HRID 456778 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@H:15]2[CH2:16][C@H:12]([C@H:13]([OH:17])[CH2:14]2)[N:11]1C(OC(C)(C)C)=O)=[O:9])#[N:2].[ClH:25]>O1CCOCC1.O>[ClH:25].[OH:17][C@H:13]1[C@H:12]2[CH2:16][C@H:15]([C@@H:10]([C:8]([N:4]3[CH2:5][CH2:6][CH2:7][C@H:3]3[C:1]#[N:2])=[O:9])[NH:11]2)[CH2:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86598896tert-Butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 24905398Asp-4000

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solid of tert-butyl (1R,3S,4S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-6-hydroxy-2-azabicyclo[2.2.1]heptane-2-carboxylate obtained in Example 42-8 (796 mg), was added a mixture of 4N hydrochloride in dioxane (1.87 mL) and water (0.13 mL). The mixture was stirred at room temperature for 5 minutes. The resulting mixture was evaporated in vacuo and the residual solid was washed with isopropyl alcohol. The solid was recrystalized from ethanol-water to give the target compound as a white crystal (367 mg)

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. washthe residual solid was washed with isopropyl alcohol
  3. customThe solid was recrystalized from ethanol-water

Sources & evidence

ORD record
ord-94894c4656a44bbe9e3970e8c317bb4e
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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