tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamate → Tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(6-iodo-3,4-dihydro-2H-chromen-4-yl)amino]propylcarbamate

HRID 898357Notes

Reaction equation

HRID 898357 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]2[C:30](=[CH:31][CH:32]=1)[O:29][CH2:28][CH2:27][CH:26]2[NH2:33]>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:33][CH:26]1[C:25]2[C:30](=[CH:31][CH:32]=[C:23]([I:22])[CH:24]=2)[O:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 9922319tert-Butyl ((S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethyl)carbamateHCID 162444196-Iodochroman-4-amine

Product 1

HCID 10325781Tert-butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(6-iodo-3,4-dihydro-2H-chromen-4-yl)amino]propylcarbamateYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An isopropyl alcohol (25 ml) solution of tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate (2.2 g, 7.2 mmol) and 6-Iodo-chroman-4-ylamine (3.0 g, 10.9 mmol) was stirred at 75° C. for 0 h. The IPA was removed in vacuo and the resulting residue dissolved in EtOAc (200 ml). The organic layer was washed with 1 N HCl (4×50 ml), followed by NaHCO3 (2×50 ml), and brine (1×50 ml). The organic layer was dried over Na2SO4 and concentrated in vacuo to yield 3.5 g (85%) of the title compound as an off white solid. MS (ESI+) for C24H29F2IN2O4 m/z 574.8 (M+H)+.

Workup

  1. customThe IPA was removed in vacuo
  2. dissolutionthe resulting residue dissolved in EtOAc (200 ml)
  3. washThe organic layer was washed with 1 N HCl (4×50 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20851533c8794a8c9f85aa2402bcdd6b
Source dataset
uspto-grants-2008_04
Patent number
US07351738B2

Reaction notes

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