Benzyl chloroformate → HCID 118117725, compound

HRID 2279939Notes

Reaction equation

HRID 2279939 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].[OH-].[Na+]>O1CCCC1.O>[CH2:25]([O:24][C:22]([NH:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)[C:3]([O:5][CH3:6])=[O:4])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 68712100HCID 68712100, compound

Product 1

HCID 118117725HCID 118117725, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-amino-2-(3-(benzyloxy)phenyl)acetate (1.09 g, 4 mmol) in a mixture of tetrahydrofuran and water (1:1, 90 mL) at 0° C. was added benzyl chloroformate (0.57 mL, 4 mmol) and aqueous sodium hydroxide (4 N, 1 mL, 4 mmol) simultaneously. The mixture was stirred at 0° C. for one hour. The ice bath was removed and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo and ethyl acetate (100 mL) and water (30 mL) were added. The layers were separated and the aqueous phase re-extracted with ethyl acetate (2×50 mL). The combined organic fractions were dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by silica gel column chromatography, eluting with 0-40% ethyl acetate in iso-hexane to afford the title compound (900 mg, 56%) as a brown oil.

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred at room temperature for 16 h
  3. customThe solvent was removed in vacuo and ethyl acetate (100 mL) and water (30 mL)
  4. additionwere added
  5. customThe layers were separated
  6. extractionthe aqueous phase re-extracted with ethyl acetate (2×50 mL)
  7. dry with materialThe combined organic fractions were dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customThe residue was purified by silica gel column chromatography
  11. washeluting with 0-40% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-9193e5fd8a8d4e1c963cbcd056c035d2
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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