Diisopropylethylamine → 4-Nitrophenyl 3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropylcarbamate

HRID 589839Notes

Reaction equation

HRID 589839 reaction equation
[O:1]([CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][NH2:22])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][CH:30]=1)=[O:27].C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>ClCCl>[O:1]([CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][NH:22][C:26](=[O:27])[O:28][C:29]1[CH:30]=[CH:31][C:32]([N+:35]([O-:37])=[O:36])=[CH:33][CH:34]=1)[Si:2]([C:15]([CH3:16])([CH3:17])[CH3:18])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 866808103-(Tert-butyldiphenylsilanoxy)-2,2-dimethylpropylamine

Product 1

HCID 665840014-Nitrophenyl 3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropylcarbamateYield 11.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution, at 0° C., of 0.120 g (3.51 mmol) of 3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropylamine in 25 ml of dichloromethane are added dropwise 1.42 g (7.03 mmol) of 4-nitrophenyl chloroformate (CAS 7693-46-1) dissolved in 5 ml of dichloromethane. 0.63 ml (3.5 mmol) of diisopropylethylamine is then added. Stirring is continued at 0° C. for 45 minutes, and the temperature of the mixture is then allowed to return to 0° C. over 1 hour. 20 ml of saturated aqueous sodium hydrogen carbonate solution are then added. The organic phase is separated out on a hydrophobic filter cartridge and the solvent is partially evaporated off under reduced pressure to a volume of about 8 ml. This solution is chromatographed on a column of silica gel, eluting with a mixture of 5 to 40% ethyl acetate in cyclohexane, to give 0.21 g of 4-nitrophenyl 3-(tert-butyldiphenylsilanoxy)-2,2-dimethylpropylcarbamate in the form of an oil.

Workup

  1. waitto return to 0° C. over 1 hour
  2. customThe organic phase is separated out on a hydrophobic filter cartridge
  3. customthe solvent is partially evaporated off under reduced pressure to a volume of about 8 ml
  4. customThis solution is chromatographed on a column of silica gel
  5. washeluting with a mixture of 5 to 40% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-26d9087db166456b9c3cebf2c79fa6a9
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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