Pentane, 1-isocyanato- → HCID 67423178, compound

HRID 880710Notes

Reaction equation

HRID 880710 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-cef93a13c3c741d4ae198f879e3f344a
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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