Ammonia → (S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamate

HRID 624885Notes

Reaction equation

HRID 624885 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.[N:32]1C=CC=CC=1.N>C(#N)C>[NH2:32][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH:14]1[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 5706350(S)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

Product 1

HCID 70082562(S)-tert-butyl 1-amino-3-cyclopropyl-1-oxopropan-2-ylcarbamateYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (S)-2-(tert-butoxycarbonylamino)-3-cyclopropylpropanoic acid (CAN 89483-06-7, 10 g, 44 mmol), di-tert-butyl dicarbonate (CAN:24424-99-5, 14.28 g, 66 mmol) and pyridine (2.4 mL) in acetonitrile (200 mL) was stirred at room temperature for 20 min. Ammonia (10 mL) was added dropwise for 20 min. The resulting reaction mixture was stirred for 4 h. During removal of most of the solvent under reduced pressure the product precipitated and the solid was filtered off and washed with acetonitrile (20 mL). The solid was dried under reduced pressure to give the title compound (7.73 g, 78%) as white solid; MS (EI): m/e 251.2 [M+Na]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 4 h
  3. customDuring removal of most of the solvent under reduced pressure the product
  4. customprecipitated
  5. filtrationthe solid was filtered off
  6. washwashed with acetonitrile (20 mL)
  7. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-3d6210924cbb44549b69d168bacf4b68
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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