Citric Acid → BOC-D-alanine

HRID 2172685Notes

Reaction equation

HRID 2172685 reaction equation
[NH2:1][C@@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[C:7]([O-:10])([O-])=[O:8].[K+].[K+].C(O)(=O)[CH2:14][C:15]([CH2:20]C(O)=O)([C:17](O)=O)O>O.CO>[C:15]([O:10][C:7]([NH:1][C@H:2]([CH3:3])[C:4]([OH:6])=[O:5])=[O:8])([CH3:20])([CH3:17])[CH3:14]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 71080D-Alanine

Product 1

HCID 637606BOC-D-alanine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a suspension of D-alanine (1 g, 11.22 mmol) in water (5.6 mL)/MeOH (2.80 mL) (2:1) K2CO3 (1.55 g, 11.22 mmol) was added at 0-5° C., followed by a solution of Boc2OO (2.61 mL, 11.22 mmol) in MeOH (2.80 mL) over 5 min. The resulting suspension was stirred for 23 h at rt. The reaction mixture was poured into water and acidified to pH=3 with aqueous citric acid solution. The white cloudy solution was extracted with DCM (3×). Organic layers were combined, washed with brine, dried over MgSO4, filtered and the solvent removed to yield 1.78 g, 9.43 mmol (R)-2-tert-butoxycarbonylamino-propionic acid.

Workup

  1. additionwas added at 0-5° C.
  2. extractionThe white cloudy solution was extracted with DCM (3×)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-9b2104c398f040b8afb3c7b1749c562c
Source dataset
uspto-grants-2015_06
Patent number
US09056843B2

Reaction notes

Loading…