Tosylmethyl isocyanide → HCID 22624692, compound

HRID 279358Notes

Reaction equation

HRID 279358 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([CH:8]([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH2:4][CH2:3]1.S([CH2:28][N+:29]#[C-])(C1C=CC(C)=CC=1)(=O)=O.CC(C)([O-])C.[K+]>C(COC)OC.C(O)(C)(C)C>[C:28]([CH:2]1[CH2:7][CH2:6][CH:5]([CH:8]([CH3:17])[CH2:9][NH:10][S:11]([CH:14]([CH3:16])[CH3:15])(=[O:13])=[O:12])[CH2:4][CH2:3]1)#[N:29]

Participants

6

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 15489190HCID 15489190, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22624692HCID 22624692, compound

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a −15° C. solution of 1 eq. of N-[2-[4-oxocyclohexyl]propyl] 2-propanesulfonamide (see Preparation 2) and 1 eq. of tosylmethyl isocyanide in dimethoxyethane is added a solution of 2.8 eq. of potassium t-butoxide in t-butanol. The cooling bath is removed and the mixture is stirred for three hours. The mixture is then diluted with water and extracted three times with diethyl ether. The combined organic extracts are dried over MgSO4, filtered and concentrated in vacuo to provide the crude material. Chromatography (silica gel) of the crude material affords the purified title compound.

Workup

  1. customThe cooling bath is removed
  2. additionThe mixture is then diluted with water
  3. extractionextracted three times with diethyl ether
  4. dry with materialThe combined organic extracts are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide the crude material

Sources & evidence

ORD record
ord-ad3ec5c56b264f8da0c09ef773c6b855
Source dataset
uspto-grants-2002_03
Patent number
US06362230B1

Reaction notes

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