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Hydrochloric Acid → (3-Cyclopropyl-1,2-oxazol-5-yl)methanamine

HRID 2105223
Notes
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Reaction equation

HRID 2105223 reaction equation
C(OC([NH:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH:15]2[CH2:17][CH2:16]2)[CH:11]=1)=O)(C)(C)C.Cl>CO>[NH2:8][CH2:9][C:10]1[O:14][N:13]=[C:12]([CH:15]2[CH2:17][CH2:16]2)[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 688156195-(tert-Butoxycarbonylaminomethyl)-3-cyclopropylisoxazole

Product 1

HCID 64156762(3-Cyclopropyl-1,2-oxazol-5-yl)methanamineYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 5-(tert-butoxycarbonylaminomethyl)-3-cyclopropylisoxazole (Method 3) (37.4 g, 0.157 mol) and 3M hydrochloric acid (80 ml) in methanol (100 ml) was heated at 50° C. for 2 hours. The methanol was removed by evaporation and aqueous residue washed with DCM. The aqueous layer was adjusted to pH 12 by careful addition of 40% aqueous sodium hydroxide solution and then extracted with DCM (×4). The extracts were combined, washed with brine, then dried (Na2SO4) and the volatiles removed by evaporation to give the title compound (11.5 g, 53%) as oil.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. customThe methanol was removed by evaporation and aqueous residue
  2. washwashed with DCM
  3. additionThe aqueous layer was adjusted to pH 12 by careful addition of 40% aqueous sodium hydroxide solution
  4. extractionextracted with DCM (×4)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customthe volatiles removed by evaporation

Sources & evidence

ORD record
ord-c818c0c7bd1c4ffab309d7af90a8cc5b
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07579349B2

Reaction notes

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