Citric Acid → HCID 68001015, compound

HRID 535340Notes

Reaction equation

HRID 535340 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1([F:19])[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:10]([OH:12])=[O:11])=[O:7])(C)(C)[CH3:2].C([O-])(O)=O.[Na+].ClC(OCC)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>Cl.O1CCOCC1>[CH2:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1([F:19])[CH2:15][CH2:16][CH2:17][CH2:18]1)[C:10]([OH:12])=[O:11])=[O:7])[CH3:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 67230265HCID 67230265, compound

Product 1

HCID 68001015HCID 68001015, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

2-tert-Butoxycarbonylamino-3-(1-fluorocyclopentyl)-propionic acid (200 mg, 0.73 mmol) was kept in 4M HCl in dioxane (3 mL) for 20 min The mixture was then freeze-dried and left under a vacuum for 2 h. The solid residue was dissolved in dioxane-H2O 1:1 (12 mL). NaHCO3 (2.18 mmol, 3 eq.) and then ethyl chloroformate (0.87 mmol 1.2 eq.) dissolved in of dioxane (1 mL) were added. The reaction mixture was stirred for 20 min until completed according LC-MS. The mixture was acidified by citric acid (10% aq.) to pH 5. The product was extracted with DCM (20 mL) and EtOAc (20 mL). The organic layers were combined, dried (MgSO4) and concentrated. The afforded crude was used without further purification in the next step.

Workup

  1. customThe mixture was then freeze-dried
  2. dissolutionThe solid residue was dissolved in dioxane-H2O 1:1 (12 mL)
  3. additionwere added
  4. extractionThe product was extracted with DCM (20 mL) and EtOAc (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe afforded crude
  8. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-6a4d3b1db3c348599f9903a47b74b774
Source dataset
uspto-grants-2014_10
Patent number
US08859505B2

Reaction notes

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