4-Nitrophenyl chloroformate → (S)-4-nitrophenyl 2-(t-butoxycarbonylamino)-3-cyclohexylpropylcarbamate

HRID 451763Notes

Reaction equation

HRID 451763 reaction equation
[NH2:1][CH2:2][C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C([O-])(O)=O.[Na+].Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26]>CC#N.C1COCC1>[N+:34]([C:31]1[CH:32]=[CH:33][C:28]([O:27][C:25]([NH:1][CH2:2][C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:4][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)=[O:26])=[CH:29][CH:30]=1)([O-:36])=[O:35]

Participants

6

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 10988904(S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate

Product 1

HCID 59382967(S)-4-nitrophenyl 2-(t-butoxycarbonylamino)-3-cyclohexylpropylcarbamateYield 67%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-tert-butyl 1-amino-3-cyclohexylpropan-2-ylcarbamate (0.65 g, 2.54 mmol) in MeCN (20 mL) and THF (5 mL) was added powdered NaHCO3 (0.43 g, 5.08 mmol) followed by a solution of p-nitrophenyl chloroformate (0.51 g, 5.08 mmol) in MeCN (20 mL) dropwise over 10 min. The mixture was stirred at rt for 2 h, filtered through a pad of Celite and concentrated to leave a white solid. This material was purified by chromatography on a 40-g silica cartridge eluted with a gradient from 0-100% EtOAc in hexanes to afford (S)-tert-butyl 1-(p-nitrophenoxycarbonylamino)-3-cyclohexylpropan-2-ylcarbamate (0.67 g, 67%) as an off-white solid.

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated
  3. customto leave a white solid
  4. customThis material was purified by chromatography on a 40-g silica cartridge
  5. washeluted with a gradient from 0-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-7fd2bf4b72664fbdb1ed8698302cf41e
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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