4-Nitrophenyl chloroformate → (4-nitrophenyl) (S)-2-(N-(tert-butoxycarbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamate

HRID 2039959Notes

Reaction equation

HRID 2039959 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][C@H:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:21]>C(Cl)Cl>[C:14]([O:13][C:12]([NH:11][C@@H:3]([CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][O:7][CH2:6]1)[CH2:2][NH:1][C:20](=[O:21])[O:22][C:23]1[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=1)=[O:18])([CH3:15])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 821294-Nitrophenyl chloroformateHCID 24812374tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate

Product 1

HCID 58011475(4-nitrophenyl) (S)-2-(N-(tert-butoxycarbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate (20.8 mg, 0.081 mmol) in anhydrous DCM (9 mL) was added 4-nitrophenyl chloroformate (17.1 mg, 0.085 mmol), followed by TEA (12.2 mg, 17 μL, 0.12 mmol). The resulting solution was stirred at rt for 5 min (monitored by LC-MS) and diluted to 12 mL. An aliquot of the carbamate mixture solution (2 mL) was used for the next step without purification.

Workup

  1. additiondiluted to 12 mL
  2. customAn aliquot of the carbamate mixture solution (2 mL) was used for the next step without purification

Sources & evidence

ORD record
ord-f9e2e2e7f12a4bfbb50d9d41a428d4b5
Source dataset
uspto-grants-2013_11
Patent number
US08580823B2

Reaction notes

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