Benzyl isocyanate → HCID 86757332, compound

HRID 651823Notes

Reaction equation

HRID 651823 reaction equation
FC1C(O)=C(F)C(F)=C(F)C=1F.[C:13]([O:17][C:18]([C@H:20]([C@@H:30]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:31]([NH:33][NH2:34])=[O:32])[CH2:21]/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH2:39]([N:46]=[C:47]=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>N1C=CC=CC=1.C(OCC)(=O)C>[C:13]([O:17][C:18]([C@H:20]([C@@H:30]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:31]([NH:33][NH:34][C:47](=[O:48])[NH:46][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:32])[CH2:21]/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 86757333HCID 86757333, compound

Product 1

HCID 86757332HCID 86757332, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.09 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-4-methylvalerohydrazide pentafluorophenol salt in 5 ml of pyridine was treated with 0.25 ml of benzyl isocyanate under a nitrogen atmosphere. The mixture was stirred for 2 hours at room temperature and then evaporated. The residue was dissolved in ethyl acetate and washed in sequence with 2M aqueous hydrogen chloride, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulphate and evaporated to give a yellow oil. This was dissolved in ethyl acetate and washed twice with 0.5% aqueous sodium hydroxide and then with saturated aqueous sodium chloride. The organic layer was again dried over anhydrous magnesium sulphate and evaporated to give 0.946 g of (E)-2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenyl-3-butenyl]-2′-(benzyl)carbamoyl-4-methylvalerohydrazide in the form of a pale yellow foam.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed in sequence with 2M aqueous hydrogen chloride, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  5. customevaporated
  6. customto give a yellow oil
  7. washwashed twice with 0.5% aqueous sodium hydroxide
  8. dry with materialThe organic layer was again dried over anhydrous magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-acf2561323d94769b02be5abfbb9752a
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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