Hydrochloric Acid → HCID 86667829, compound

HRID 539067Notes

Reaction equation

HRID 539067 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH:17]1[CH2:19][CH2:18]1)[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH:17]1([CH2:16][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13][OH:14])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54104350HCID 54104350, compound

Product 1

HCID 86667829HCID 86667829, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-2-(benzyloxycarbonylamino)-3-cyclopropylpropanoic acid (0.292 g, 1.11 mmol) in THF (2 mL) was cooled to 0° C. and treated with borane-THF complex (1.44 mL, 1.44 mmol). The mixture was stirred at ambient temperature for 4 hours and then treated with 1N HCl until bubbling ceased. After stirring at ambient temperature overnight, the organic solvent was concentrated. The residue is treated with EtOAc, aqueous phase removed, organic phase washed with 1N NaOH, dried (phase separator silicone treated filter paper), concentrated to provide (S)-benzyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate (0.156 g, 56% yield) as a white gum.

Workup

  1. additiontreated with borane-THF complex (1.44 mL, 1.44 mmol)
  2. customuntil bubbling
  3. stirringAfter stirring at ambient temperature overnight
  4. concentrationthe organic solvent was concentrated
  5. additionThe residue is treated with EtOAc, aqueous phase
  6. customremoved
  7. washorganic phase washed with 1N NaOH
  8. customdried
  9. addition(phase separator silicone treated filter paper)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9203a267181a40f080d748854f4c89a1
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

Loading…