Sodium Carbonate → benzyl 3-(1-amino-5-cyano-1H-pyrrol-2-yl)azetidine-1-carboxylate

HRID 1972945Notes

Reaction equation

HRID 1972945 reaction equation
C(OC([NH:8][N:9]1[C:13]([C:14]#[N:15])=[CH:12][CH:11]=[C:10]1[CH:16]1[CH2:19][N:18]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:17]1)=O)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CO.O1CCOCC1>[NH2:8][N:9]1[C:13]([C:14]#[N:15])=[CH:12][CH:11]=[C:10]1[CH:16]1[CH2:17][N:18]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:19]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 58529525benzyl 3-(1-[(tert-butoxycarbonyl)amino]-5-cyano-1H-pyrrol-2-yl]azetidine-1-carboxylate

Product 1

HCID 58529445benzyl 3-(1-amino-5-cyano-1H-pyrrol-2-yl)azetidine-1-carboxylateYield 96.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of benzyl 3-{1-[(tert-butoxycarbonyl)amino]-5-cyano-1H-pyrrol-2-yl}azetidine-1-carboxylate (800 mg, 2.02 mmol) in methanol (2.5 mL) was added a solution of 4 M HCL in dioxane (2.5 mL). The reaction was stirred (0° C.) for 15 min, then was allowed to warm to rt. After 4 h, the reaction was recooled (0° C.) and the mixture was made basic (pH 9) with slow addition of 2M aqueous Na2CO3. The mixture was allowed to warm to rt and was extracted with EtOAc (3×20 mL). The combined organics were washed with brine, dried (Na2SO4), and evaporated to afford 575 mg (96%) of the desired product, which was used without further characterization.

Workup

  1. temperatureto warm to rt
  2. waitAfter 4 h
  3. custom(0° C.)
  4. temperatureto warm to rt
  5. extractionwas extracted with EtOAc (3×20 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-415d8e4c4d6d44f885524a75628d06e0
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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