Hydrochloric Acid → HCID 59526017, compound

HRID 385821Notes

Reaction equation

HRID 385821 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[N:20]=1)[CH2:12][C:13]([O:15]CC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO.C(O)(C)(C)C>[CH2:1]([O:8][C:9]([N:11]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Br:25])[N:20]=1)[CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59526023HCID 59526023, compound

Product 1

HCID 59526017HCID 59526017, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl N-[(benzyloxy)carbonyl]-N-[(6-bromopyridin-2-yl)methyl]glycinate (0.21 g, 0.52 mmol) was dissolved in methanol (5.1 mL) and tert-butanol (5.1 mL). Potassium hydroxide (2.6 mL, 2.60 mmol) was added and the reaction was heated at 60° C. for two hours. The reaction was made acidic with 1M hydrochloric acid and the product extracted with ethyl acetate. The organic layer was then dried over magnesium sulfate, filtered and concentrated. The product was used without further purification to yield the title compound.

Workup

  1. extractionthe product extracted with ethyl acetate
  2. dry with materialThe organic layer was then dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was used without further purification

Sources & evidence

ORD record
ord-bf48a0f94b0644748491960465ecb0de
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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