Diisopropylcarbodiimide → HCID 57951456, compound

HRID 1013344Notes

Reaction equation

HRID 1013344 reaction equation
C(N=C=NC(C)C)(C)C.[CH3:10][C:11]1[CH2:15][C:14]2([CH2:20][CH2:19][CH:18]([C:21]([OH:23])=O)[CH2:17][CH2:16]2)[O:13][N:12]=1.O.O[N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2N=N1.[C:35](NC1C=CC=CC=1)([CH3:38])([CH3:37])[CH3:36]>C(Cl)Cl>[C:35]([C:33]1[CH:32]=[CH:31][C:30]([NH:26][C:21]([CH:18]2[CH2:17][CH2:16][C:14]3([O:13][N:12]=[C:11]([CH3:10])[CH2:15]3)[CH2:20][CH2:19]2)=[O:23])=[CH:29][CH:34]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 57951454HCID 57951454, compound

Product 1

HCID 57951456HCID 57951456, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N′-diisopropylcarbodiimide (96 mg, 0.76 mmol) was added to a solution of 3-methyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxylic acid (150 mg, 0.76 mmol) in DCM (40 ml). The reaction mixture was mixed after 30 minutes with 1-hydroxybenzotriazole hydrate (HOBt, 101 mg, 0.76 mmol) and tert-butylaniline (113 mg, 0.76 mmol), stirred overnight and the solvent removed under vacuum. The residue was taken up in EtOAc. The organic phase was washed successively with diluted aq. citric acid solution and sat. aq. NaCl solution, dried over magnesium sulphate and the solvent removed under vacuum. The desired product N-(4-tert-butylphenyl)-3-methyl-1-oxa-2-azaspiro[4.5]dec-2-ene-8-carboxamide was obtained after purification by column chromatography (SiO2, hexane/EtOAc 1:1) as a diastereomer mixture in a yield of 66 mg.

Workup

  1. customthe solvent removed under vacuum
  2. washThe organic phase was washed successively with diluted aq. citric acid solution and sat. aq. NaCl solution
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-b315e5b1a3bc4e61b73b48b61bc8e967
Source dataset
uspto-grants-2011_07
Patent number
US07981883B2

Reaction notes

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