1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 54419005, compound

HRID 965144Notes

Reaction equation

HRID 965144 reaction equation
[CH3:1][CH:2]([CH3:33])[CH2:3][CH:4]([C:9](=[O:32])[NH:10][C@H:11]1[CH2:29][C:28]2=[CH:30][N:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=32)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:31])[CH2:5][C:6]([OH:8])=O.O.OC1C=CC2NN=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:56]([O:63][NH2:64])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>CN(C=O)C>[CH2:56]([O:63][NH:64][C:6](=[O:8])[CH2:5][CH:4]([C:9](=[O:32])[NH:10][C@H:11]1[CH2:29][C:28]2=[CH:30][N:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=32)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:31])[CH2:3][CH:2]([CH3:1])[CH3:33])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 102313O-BenzylhydroxylamineHCID 54460498(11S)-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanoic acidHCID 178526938HCID 178526938, compound

Product 1

HCID 54419005HCID 54419005, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the less polar stereoisomer of (11S)-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19 ]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl)hexanoic acid (210 mg) and 5-hydroxybenzotriazole monohydrate (109 mg) in anhydrous DMF (20 mL) under argon was cooled to 0° C. (ice bath). To this mixture was added EDCI (282 mg) and stirring was continued for 0.5 hours. O-benzylhydroxylamine (0.27 mL) was added to the solution and the reaction mixture was left to warm to room temperature overnight. All volatiles were removed under reduced pressure. The residue was taken up in CH2 Cl2 (100 mL) and 20% HCl (100 mL) and transferred to a separatory funnel. The organic phase was isolated and the aqueous phase washed (2×100 mL) with CH2Cl2. The organic materials were then washed consecutively with 5% NaHCO3, brine, dried (MgSO4), filtered and concentrated to provide (11S)-N-benzyloxy-5-methyl-3-(10-oxo-1,9-diazatricyclo[11.6.1.014,19 ]eicosa-13(20),14(19),15,17-tetraen-11-ylcarbamoyl) hexanamide as a crystalline product. The product was further purified by column chromatography on silica gel followed by crystallization from hot ethyl acetate/CH2Cl2, to provide the more polar stereoisomer of the compound having a melting point at 232°-233° C. m.p., and the less polar stereoisomer of the compound having a melting point at 251°-253° C.

Workup

  1. waitthe reaction mixture was left
  2. customAll volatiles were removed under reduced pressure
  3. custom20% HCl (100 mL) and transferred to a separatory funnel
  4. customThe organic phase was isolated
  5. washthe aqueous phase washed (2×100 mL) with CH2Cl2
  6. washThe organic materials were then washed consecutively with 5% NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f025922c904f4c71a735f3c56cb7c310
Source dataset
uspto-grants-1998_06
Patent number
US05773428

Reaction notes

Loading…