1-Hydroxybenzotriazole → HCID 437008, compound

HRID 1978052Notes

Reaction equation

HRID 1978052 reaction equation
C([C@H]([C@@H:14]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:15]([NH:17][N:18](S(C)(=O)=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])CCCC1C=CC=CC=1)(O)=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CC([Si](ON)(C)C)(C)C>CN(C)C=O>[CH3:31][CH:30]([CH3:32])[CH2:29][CH2:14][C:15]([NH:17][NH:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 15380762HCID 15380762, compound

Product 1

HCID 437008HCID 437008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.165 g of 2(R)-[1(S)-(carboxy)-4-phenylbutyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in 4 ml of dry dimethylformamide was cooled to 0° C. while stirring under nitrogen and 0.09 g of 1-hydroxybenzotriazole and 0.09 g of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride were added in succession. After stirring for 40 minutes at 0° C. the solution was treated with 0.18 g of 0-(tert-butyldimethylsilyl)hydroxylamine and the mixture was left to come to room temperature and then stirred overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and 5% aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was washed in succession with water, 2M sulphuric acid, water and brine and then dried over anhydrous magnesium sulphate. The solvent was evaporated to give a pale pink gum which on crystallization from ether gave 0.05 g of 2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-2′-methanesulphonyl)-4-methyl-2′phenylvalerohydrazide in the form of an off-white solid.

Workup

  1. stirringAfter stirring for 40 minutes at 0° C. the solution
  2. waitthe mixture was left
  3. customto come to room temperature
  4. stirringstirred overnight
  5. customThe solvent was evaporated
  6. customthe residue was partitioned between ethyl acetate and 5% aqueous sodium hydrogen carbonate solution
  7. washThe ethyl acetate layer was washed in succession with water, 2M sulphuric acid, water and brine
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customThe solvent was evaporated
  10. customto give a pale pink gum which
  11. customon crystallization from ether

Sources & evidence

ORD record
ord-e1b5040700fe496e9bdd7f5944134477
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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