Ethyl orthoformate → HCID 67517239, compound

HRID 2173386Notes

Reaction equation

HRID 2173386 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[F:12].[CH:13](OCC)(OCC)OCC.[N-:23]=[N+:24]=[N-:25].[Na+]>CC(O)=O>[F:12][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:7][C:2]=1[N:1]1[CH:13]=[N:25][N:24]=[N:23]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 27783244-Amino-3-fluorophenylacetic acid

Product 1

HCID 67517239HCID 67517239, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of (4-amino-3-fluorophenyl)acetic acid (450 mg, 2.66 mmol) and triethyl orthoformate (1.18 g, 7.98 mmol) in HOAc (10 mL) was added sodium azide (208 mg, 3.19 mmol), and the mixture was heated to 100° C. for 3 hours. After the reaction was completed, the reaction mixture was cooled to ambient temperature. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was directly used in next step.

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8efdf79b83ab4d0eaed2e75c9aea0b78
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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