Acetic Acid → HCID 131714196, compound

HRID 1981409Notes

Reaction equation

HRID 1981409 reaction equation
N#N.C(NC(C1C=CC=CC=1)CC(O)CC(CCCNC(OCC1C=CC=CC=1)=O)[C@@H](C(N1CCC[C@H]1C(OCC1C=CC=CC=1)=O)=O)NC(OCC1C=CC=CC=1)=O)(=O)C1C=CC=CC=1.[ClH:67].[C:68]([NH:76][C@@H:77]([CH2:98][C:99]1[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=1)[CH:78]([OH:97])[CH2:79][NH:80][C@H:81]([C:87]([N:89]1[CH2:96][CH2:95][CH2:94][C@H:90]1[C:91]([OH:93])=[O:92])=[O:88])[CH2:82][CH2:83][CH2:84][CH2:85][NH2:86])(=[O:75])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1.C(O)CCC.C(O)(=O)C>C(O)C.[Pd].O>[ClH:67].[ClH:67].[C:68]([NH:76][C@@H:77]([CH2:98][C:99]1[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=1)[CH:78]([OH:97])[CH2:79][NH:80][C@H:81]([C:87]([N:89]1[CH2:96][CH2:95][CH2:94][C@H:90]1[C:91]([OH:93])=[O:92])=[O:88])[CH2:82][CH2:83][CH2:84][CH2:85][NH2:86])(=[O:75])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 2631-ButanolHCID 131714197HCID 131714197, compoundHCID 131714199HCID 131714199, compound

Product 1

HCID 131714196HCID 131714196, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of the ester product from part (e) (0.55 g., 0.64 mmole) in 95% ethanol (50 ml.) containing 10% palladium on carbon catalyst (0.2 g.) is hydrogenated under atmospheric pressure overnight. The catalyst is filtered, washed with 95% ethanol, and the filtrate and the washings are concentrated into an oily residue. This is treated for 5 minutes with 1.4N hydrochloric acid/acetic acid (10 ml.). The reaction mixture is concentrated under reduced pressure and the residue triturated with ether to yield 0.31 g. of an off-white solid residue. This crude product is purified on an HP-20 column (5% methanol/0.01N hydrochloric acid→90% methanol/0.01N hydrochloric acid) to give 0.08 g. of (3S)-1-[N-[3-(benzoylamino)-2-hydroxy-4-phenylbutyl]-L-lysyl]-L-proline, hydrochloride as a white solid; m.p. 67°-80°. Rf 0.15 (silica gel; n-butanol:acetic acid:water; 3:1:1).

Workup

  1. customis hydrogenated under atmospheric pressure overnight
  2. filtrationThe catalyst is filtered
  3. washwashed with 95% ethanol
  4. concentrationthe filtrate and the washings are concentrated into an oily residue
  5. additionThis is treated for 5 minutes with 1.4N hydrochloric acid/acetic acid (10 ml.)
  6. concentrationThe reaction mixture is concentrated under reduced pressure
  7. customthe residue triturated with ether
  8. customto yield 0.31 g
  9. customThis crude product is purified on an HP-20 column (5% methanol/0.01N hydrochloric acid→90% methanol/0.01N hydrochloric acid)
  10. customto give 0.08 g

Sources & evidence

ORD record
ord-2314ba547afb47f3aee41a9ae053b72f
Source dataset
uspto-grants-1985_04
Patent number
US04514391

Reaction notes

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