HCID 58784286, compound → HCID 58784309, compound

HRID 1374686Notes

Reaction equation

HRID 1374686 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[N:10]([CH2:19][CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH3:23])[C:9]([O:31]C)=[N:8][C:7]=1[CH2:33][O:34][CH2:35][CH2:36][N:37]=[N+:38]=[N-:39])=[O:5])[CH3:2]>C(Cl)Cl.FC(F)(F)C(O)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[N:10]([CH2:19][CH2:20][CH2:21][NH:22][CH3:23])[C:9](=[O:31])[NH:8][C:7]=1[CH2:33][O:34][CH2:35][CH2:36][N:37]=[N+:38]=[N-:39])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 58784286HCID 58784286, compound

Product 1

HCID 58784309HCID 58784309, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of racemic 4-(2-azido-ethoxymethyl)-1-[3-(tert-butoxycarbonyl-methyl-amino)-propyl]-6-(2-chloro-phenyl)-2-methoxy-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester (200 mg, 0.354 mmol) in CH2Cl2 (3 mL) and trifluoroacetic acid (1.5 mL) was stirred at RT under N2 to remove the BOC protecting group. After 2 h, 1N aqueous HCl (1 mL) and THF (3 mL) was added to the mixture. The mixture was left to stir overnight. The mixture was taken up in EtOAc (50 mL) and basicified with saturated NaHCO3 solution. The organic extract was washed with brine (25 mL), dried (Na2SO4), filtered, concentrated and dried in vacuo 150 mg (93% crude yield) of thick yellowish oil as crude product.

Workup

  1. customto remove the BOC protecting group
  2. addition1N aqueous HCl (1 mL) and THF (3 mL) was added to the mixture
  3. waitThe mixture was left
  4. extractionThe organic extract
  5. washwas washed with brine (25 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried in vacuo 150 mg (93% crude yield) of thick yellowish oil as crude product

Sources & evidence

ORD record
ord-4de745bfb3a544ba9e3d5c0a67d0d757
Source dataset
uspto-grants-2007_01
Patent number
US07166603B2

Reaction notes

Loading…