(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 451983Notes

Reaction equation

HRID 451983 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-cd7b64bfd3f14fa8ab841789d19bba8b
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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