Sodium Hydroxide → (R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acid

HRID 2201079Notes

Reaction equation

HRID 2201079 reaction equation
[NH2:1][C@H:2]([CH2:6][CH:7]1[CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4].[OH-].[Na+].[C:12](=O)([O:18]C(C)(C)C)[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]>C(O)C.O.C1COCC1>[C:14]([O:13][C:12]([NH:1][C@H:2]([CH2:6][CH:7]1[CH2:9][CH2:8]1)[C:3]([OH:5])=[O:4])=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 9209421D-CyclopropylalanineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 2756015(R)-2-((tert-Butoxycarbonyl)amino)-3-cyclopropylpropanoic acidYield 56.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-amino-3-cyclopropylpropanoic acid (1.0 g, 7.7.4 mmol) in Ethanol (15 mL) and water (8 mL) was added 1N NaOH (10 mL) and Di-tert-butyl carbonate (1.86 g, 8.52 mmol) in THF (8 mL). After stirring at room temperature for 15 h, the solution was diluted with water, extracted with ether, the aqueous layer was separated and was acidified to pH 2 with conc. HCl, the aqueous layer was extracted with EtOAc, organic layer was separated, washed with brine, dried and concentrated to give (R)-2-(tert-butoxycarbonylamino)-3-cyclopropylpropanoic acid (1.0 g).

Workup

  1. extractionextracted with ether
  2. customthe aqueous layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc, organic layer
  4. customwas separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f4ac31c7757041a9b67706a4c185bb2a
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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