Pentane, 1-isocyanato- → HCID 67423178, compound

HRID 2070059Notes

Reaction equation

HRID 2070059 reaction equation
[CH2:1]([N:6]=[C:7]=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].FC(F)(F)C(O)=O.[CH2:16]([O:23][C:24]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:26][C:25]=1[CH:38]1[CH2:41][NH:40][CH2:39]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1.C(N(CC)C(C)C)(C)C>[CH2:1]([NH:6][C:7]([N:40]1[CH2:41][CH:38]([C:25]2[CH:26]=[CH:27][C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:29][C:24]=2[O:23][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:39]1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 206036Pentane, 1-isocyanato-HCID 67423431HCID 67423431, compound

Product 1

HCID 67423178HCID 67423178, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 81531DiisopropylethylamineSolvent

Procedure

In a 10 ml round-bottomed flask, 0.15 g of 3-(2,4-bis(benzyloxy)phenyl)azetidine trifluoroacetate is dissolved in 3 ml of tetrahydrofuran in the presence of 0.1 ml of N,N-diisopropylethylamine. 0.04 ml of pentyl isocyanate is added and the reaction mixture is then stirred for 20 minutes at ambient temperature. The reaction mixture is extracted with ethyl acetate and the organic phases are then combined and dried over magnesium sulphate. The residue is chromatographed on silica gel (9/1 heptane/ethyl acetate). 0.1 g of 3-(2,4-bis(benzyloxy)phenyl)azetidine-1-carboxylic acid pentylamide is obtained. Yield=67%.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. customThe residue is chromatographed on silica gel (9/1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-03152fc54e224bd0893e66cdd4a09070
Source dataset
uspto-grants-2012_10
Patent number
US08299259B2

Reaction notes

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