Triethylamine → HCID 86673843, compound

HRID 1527396Notes

Reaction equation

HRID 1527396 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([F:15])([CH2:13]O)[CH2:10][C@H:9]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.CS(Cl)(=O)=O.[N-:38]=[N+:39]=[N-:40].[Na+]>C(Cl)Cl.CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:13][N:38]=[N+:39]=[N-:40])([F:15])[CH2:10][C@H:9]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 68283350HCID 68283350, compound

Product 1

HCID 86673843HCID 86673843, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-4-fluoro-4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester (1.76 g, 4.98 mmol) in CH2Cl2 (30 mL) and few drops of NEt3 was stirred at RT for 10 min then methanesulfonyl chloride (0.39 mL, 5.03 mmol) was added. The reaction was stirred at RT for 30 min then poured into water and extracted with EtOAc. The organic layer was dried with Na2SO4, filtered and concentrated. The residue (2.25 g, 4.21 mmol) was dissolved in DMF (50 mL) and sodium azide (1.69 g, 26.1 mmol) was added. The solution was stirred for 16 hours at 80° C. then was cooled to RT, poured into water and extracted with EtOAc. The organic layer was dried with Na2SO4, filtered and concentrated. Purification by flash column chromatography on silica gel (c-hexane/EtOAc 1:1). MS (UPLC/MS): 379 [M+H]+; tR (HPLC conditions f): 2.44 min.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. stirringThe solution was stirred for 16 hours at 80° C.
  6. temperaturethen was cooled to RT
  7. extractionextracted with EtOAc
  8. dry with materialThe organic layer was dried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by flash column chromatography on silica gel (c-hexane/EtOAc 1:1)
  12. custom2.44 min.

Sources & evidence

ORD record
ord-398784a901934fa1be93ba1d5411721f
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…