Sodium Azide → HCID 20605700, compound

HRID 497412Notes

Reaction equation

HRID 497412 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:15]2[C:14](=[O:16])[CH2:13][CH2:12][CH2:11][C:10]=2[NH:9][CH:8]=1)=[O:6])[CH2:2][CH3:3].[N-:17]=[N+]=[N-].[Na+]>FC(F)(F)C(O)=O.O>[CH2:1]([O:4][C:5]([C:7]1[C:15]2[C:14](=[O:16])[NH:17][CH2:13][CH2:12][CH2:11][C:10]=2[NH:9][CH:8]=1)=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 33557Sodium Azide2×HCID 20605698HCID 20605698, compound

Product 1

HCID 20605700HCID 20605700, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid propyl ester (2.0 g) and NaN3 (2.0 g) in 50 mL of trifluoroacetic acid is stirred at 60-80° C. for a period of 3 days during which additional 2.5 g NaN3 of is added on first, second and third day. After diluted with water, the mixture is extracted with Ethyl acetate. The extract is washed with NaHCO3, brine and concentrated under reduced pressure. The residue is subject to a silica gel chromatography eluting with 10% MeOH in CH2Cl2 to give 500 mg of 4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-3-carboxylic acid propyl ester as a foam.

Workup

  1. additionof is added on first, second and third day
  2. extractionthe mixture is extracted with Ethyl acetate
  3. washThe extract is washed with NaHCO3, brine
  4. concentrationconcentrated under reduced pressure
  5. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-010307c7a15547f780ea3e18ba08614d
Source dataset
uspto-grants-2005_09
Patent number
US06949562B2

Reaction notes

Loading…