Cyclopropylamine → tert-Butyl ((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)carbamate

HRID 1928700Notes

Reaction equation

HRID 1928700 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:19][CH2:20][CH3:21])[C@H:14]([OH:18])[C:15](O)=[O:16])=[O:11])([CH3:8])([CH3:7])[CH3:6].C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.Cl>C(OCC)(=O)C>[CH:1]1([NH:4][C:15](=[O:16])[C@@H:14]([OH:18])[C@@H:13]([NH:12][C:10]([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11])[CH2:19][CH2:20][CH3:21])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 29928234(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid

Product 1

HCID 68950941tert-Butyl ((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Cyclopropylamine (55 mg, 0.97 mmol) was dropwise added to an ethyl acetate (5 mL) solution of (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid (200 mg, 0.81 mmol), and the mixture was cooled by ice. HOBt monohydrate (130 mg, 0.85 mmol) and EDC hydrochloride (171 mg, 0.89 mmol) were added thereto, and the mixture was stirred with cooling by ice. As a result, the solid in the mixture aggregated to form a hard lump after about 5 minutes, and the mixture became impossible to be stirred.

Workup

  1. temperaturethe mixture was cooled by ice
  2. temperaturewith cooling by ice
  3. customto form a hard lump after about 5 minutes
  4. stirringto be stirred

Sources & evidence

ORD record
ord-6b5bd5cd7e7f4618914f832452574da7
Source dataset
uspto-grants-2012_05
Patent number
US08183413B2

Reaction notes

Loading…