Acetonitrile → HCID 59772987, compound

HRID 2220686Notes

Reaction equation

HRID 2220686 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][N:14]([C:26](=[O:37])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)=O)(C)(C)C.C(=O)(O)[O-].[Na+].C(#N)C>ClCCl.FC(F)(F)C(O)=O>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[O:33][CH3:34])[C:26]([N:14]([CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)[CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)=[O:37]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 68669020HCID 68669020, compound

Product 1

HCID 59772987HCID 59772987, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent2×

Procedure

In 20 mL mixture of dichloromethane and trifluoroacetic acid 30%, was dissolved 2-{[(3,4-Dimethoxy-benzoyl)-naphthalen-2-ylmethyl-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester 1.1 g (2.18 mmol). After 1 hour at room temperature, saturated solution of sodium bicarbonate was added until basic pH, the mixture was extracted with dichlorometane, dried over magnesium sulfate, filtered and concentrated under vacuum, yield to 0.88 g. LC-MSD, m/z for: C25H28N2O3 [M+H]: 404.2. LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 7 minutes: 1.37 min.

Workup

  1. extractionthe mixture was extracted with dichlorometane
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customyield to 0.88 g
  6. custom1.37 min.

Sources & evidence

ORD record
ord-b993bafcc4ca469cac3fe4ea5b9fa2d7
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

Loading…