Benzoyl chloride → HCID 53871092, compound

HRID 1085012Notes

Reaction equation

HRID 1085012 reaction equation
[CH2:1]([O:3][P:4]([CH2:24][NH:25][C:26]([C@@H:28]([NH:33][C:34]([C@@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1C(OCC1C=CC=CC=1)=O)=[O:35])[CH2:29][CH:30]([CH3:32])[CH3:31])=[O:27])([CH2:6][CH:7]([C:12](=[O:23])[NH:13][C@H:14]([C:19](=[O:22])[NH:20][CH3:21])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:5])[CH3:2].C(N(CC)CC)C.[C:58](Cl)(=[O:65])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1>C(O)C.Cl.ClCCl.[Pd]>[CH2:1]([O:3][P:4]([CH2:24][NH:25][C:26](=[O:27])[C@H:28]([CH2:29][CH:30]([CH3:32])[CH3:31])[NH:33][C:34](=[O:35])[C@@H:36]1[CH2:40][CH2:39][CH2:38][N:37]1[C:58](=[O:65])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([CH2:6][CH:7]([C:12](=[O:23])[NH:13][C@H:14]([C:19](=[O:22])[NH:20][CH3:21])[CH2:15][CH:16]([CH3:17])[CH3:18])[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 53849901HCID 53849901, compound

Product 1

HCID 53871092HCID 53871092, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.36 g of benzyl(S)-2-[[(S)-1-[[[ethoxy[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinyl]methyl]carbamoyl]-3-methylbutyl]carbamoyl]-1-pyrrolidinecarboxylate was dissolved in 5 ml of ethanol containing 0.5 ml of 1 M hydrochloric acid. The solution was hydrogenated over 5% palladium-on-charcoal for 2 hours. After filtration and evaporation of the filtrate, the residue was re-evaporated with toluene until a white solid was obtained. This solid was dissolved in 6 ml of dichloromethane. The solution was cooled to 0° C. and treated with 0.15 ml of triethylamine and 0.064 ml of benzoyl chloride. The mixture was stirred at room temperature for 16 hours and the solvent was then removed by evaporation. The residue was dissolved in ethyl acetate. The mixture was filtered and the filtrate was evaporated to give a pale yellow gum. Chromatography on silica gel using 3% ethanol in chloroform for the elution followed by evaporation yielded 0.32 g of [[ [N-(1-benzoyl-L-prolyl)-L-leucyl]amino]methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester in the form of a white foam.

Workup

  1. filtrationAfter filtration and evaporation of the filtrate
  2. customthe residue was re-evaporated with toluene until a white solid
  3. customwas obtained
  4. customthe solvent was then removed by evaporation
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. filtrationThe mixture was filtered
  7. customthe filtrate was evaporated
  8. customto give a pale yellow gum
  9. washChromatography on silica gel using 3% ethanol in chloroform for the elution
  10. customfollowed by evaporation

Sources & evidence

ORD record
ord-af07637922584f3092ae813251ac4d69
Source dataset
uspto-grants-1991_04
Patent number
US05006651

Reaction notes

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