[1-(Cyclopropylcarbamoylhydroxymethyl)cyclopropyl]carbamic acid tert-butyl ester → 2-(1-aminocyclopropyl)-N-cyclopropyl-2-hydroxyacetamide

HRID 642897Notes

Reaction equation

HRID 642897 reaction equation
C(OC(=O)[NH:7][C:8]1([CH:11]([C:13](=[O:18])[NH:14][CH:15]2[CH2:17][CH2:16]2)[OH:12])[CH2:10][CH2:9]1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][C:8]1([CH:11]([OH:12])[C:13]([NH:14][CH:15]2[CH2:16][CH2:17]2)=[O:18])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 67385903[1-(Cyclopropylcarbamoylhydroxymethyl)cyclopropyl]carbamic acid tert-butyl ester

Product 1

HCID 575620962-(1-aminocyclopropyl)-N-cyclopropyl-2-hydroxyacetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [1-(cyclopropylcarbamoylhydroxymethyl)cyclopropyl]carbamic acid tert-butyl ester in CH2Cl2 (5 mL) and TFA (5 mL) was stirred at room temperature for 2.5 h. The reaction mixture was concentrated and chased with toluene to yield 2-(1-aminocyclopropyl)-N-cyclopropyl-2-hydroxyacetamide.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-391111a1fd634781b8c9b37d7b30cbae
Source dataset
uspto-grants-2010_04
Patent number
US07696250B2

Reaction notes

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