Acetic Acid → 4-Nitrophenyl hydrogen carbonimidate

HRID 705175Notes

Reaction equation

HRID 705175 reaction equation
C(SCCCCCC[NH2:27])(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:30].CCN(C(C)C)C(C)C.C(O)(=O)C>C1COCC1>[C:29](=[O:30])([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)[NH2:27]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 21182578HCID 21182578, compound

Product 1

HCID 1699564-Nitrophenyl hydrogen carbonimidateYield 69.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(Tritylthio)hexane-1-amine (1.21 g, 3.22 mmol) and p-nitrophenyl chloroformate (0.78 g, 3.86 mmol) were suspended in dry THF (15 mL). DIEA (841 μL, 4.83 mmol) was added, and the resulting solution was stirred at room temperature for 2 h. After acidification by addition of acetic acid the solvent was evaporated under reduced pressure, and the residue was purified by RP-HPLC. 1.21 g (2.25 mmol) p-nitrophenyl carbamate were obtained after lyophilisation.

Workup

  1. customwas evaporated under reduced pressure
  2. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-ddb049d3ecf3459cae7e455aae0ecb09
Source dataset
uspto-grants-2015_11
Patent number
US09173953B2

Reaction notes

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