3-Iodobenzylamine → 1-tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-iodobenzyl)amino]propylcarbamate

HRID 857259Notes

Reaction equation

HRID 857259 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]2[CH2:13][O:12]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[I:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27].FC1C=C(C[C@H](NC(=O)OCC2C=CC=CC=2)[C@H]2CO2)C=C(F)C=1>C(O)(C)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:11]([OH:12])[CH2:13][NH:27][CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([I:22])[CH:24]=1

Participants

5

Reactant 3

HCID 970123-IodobenzylamineHCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamateHCID 10131699HCID 10131699, compound

Product 1

HCID 161093481-tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-iodobenzyl)amino]propylcarbamate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, PREPARATION 3, 1.75 g, 5.8 mmole) is mixed with isopropanol (30 ml). The reaction flask is charged with 3-iodobenzylamine (VI). The reaction mixture is heated to reflux for 45 minutes, HPLC analysis indicates complete disappearance of the epoxide (V). The reaction mixture is concentrated under reduced pressure and the residue is partitioned between ethyl acetate (150 ml) and aqueous hydrochloric acid (3%, 35 ml). The organic phase is separated and washed with aqueous hydrochloric acid (3%, 20 ml), bicarbonate, saline and dried over sodium sulfate. Concentration under reduced pressure gives the title compound, M+H=535.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 45 minutes
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customthe residue is partitioned between ethyl acetate (150 ml) and aqueous hydrochloric acid (3%, 35 ml)
  5. customThe organic phase is separated
  6. washwashed with aqueous hydrochloric acid (3%, 20 ml), bicarbonate, saline
  7. dry with materialdried over sodium sulfate
  8. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-881a014510ca4361b09454574dfd49ed
Source dataset
uspto-grants-2006_12
Patent number
US07144897B2

Reaction notes

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