(4-nitrophenyl) (S)-2-(N-(tert-butoxycarbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamate → methyl 2-((R)-((R)-1-((S)-2-(Boc-amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamate

HRID 218445Notes

Reaction equation

HRID 218445 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][C@H:25]1[CH2:30][CH2:29][CH2:28][O:27][CH2:26]1)[CH2:10][NH:11][C:12](=[O:23])OC1C=CC([N+]([O-])=O)=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:32](C(F)(F)F)=O.[Cl:38][C:39]1[CH:40]=[C:41]([C@@H:45]([C@@H:53]2[CH2:58][CH2:57][CH2:56][NH:55][CH2:54]2)[O:46][CH2:47][CH2:48][NH:49][C:50](=[O:52])[OH:51])[CH:42]=[CH:43][CH:44]=1>>[C:6]([NH:8][C@@H:9]([CH2:24][C@H:25]1[CH2:30][CH2:29][CH2:28][O:27][CH2:26]1)[CH2:10][NH:11][C:12]([N:55]1[CH2:56][CH2:57][CH2:58][C@@H:53]([C@H:45]([C:41]2[CH:42]=[CH:43][CH:44]=[C:39]([Cl:38])[CH:40]=2)[O:46][CH2:47][CH2:48][NH:49][C:50](=[O:51])[O:52][CH3:32])[CH2:54]1)=[O:23])([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

3

Reactant 2

HCID 58011475(4-nitrophenyl) (S)-2-(N-(tert-butoxycarbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamateHCID 1317297722-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate TFA salt

Product 1

HCID 58011512methyl 2-((R)-((R)-1-((S)-2-(Boc-amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamateYield 63%

Procedure

To (4-nitrophenyl) (S)-2-(N-(tert-butoxycarbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamate solution (2 mL, 0.013 mmol) was added 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate TFA salt (7.0 mg, 0.016 mmol), followed by excess TEA (0.3 mL). The mixture was stirred for 30 min, then the solvent was removed in vacuo. The resulting oil was purified on preparative HPLC to give methyl 2-((R)—((R)-1-((S)-2-(Boc-amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamate 5 mg, yield 63%. MS ESI+ve m/z 611 (M+H).

Workup

  1. customthe solvent was removed in vacuo
  2. customThe resulting oil was purified on preparative HPLC

Sources & evidence

ORD record
ord-b89e25fe103f4990b1e30ac90a1494d9
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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