HCID 86753148, compound → HCID 14801625, compound

HRID 2395153Notes

Reaction equation

HRID 2395153 reaction equation
C(OC(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(NC[C:67]1[C:80](OC)=[CH:79][CH:78]=[C:77]2[C:68]=1[O:69][C:70]1[C:71]([CH2:87][C:88]([O:90]CC3C=CC=CC=3)=[O:89])=[C:72](OC)[CH:73]=[CH:74][C:75]=1[C:76]2(C)C)=O)C)=O)CC(C)C)=O)C)=O)CC(C)C)=O)CC1C=CC=CC=1)=O)C)=O)C)=O)C(C)C)=O)C1C=CC=CC=1.COC1C=CC2C(C)(C)C3C(OC=2C=1CC([O-])=O)=CC(OC)=CC=3>FC(F)(F)C(O)C(F)(F)F.[Pd]>[CH:74]1[C:75]2[CH2:76][C:77]3[C:68](=[CH:67][CH:80]=[CH:79][CH:78]=3)[O:69][C:70]=2[C:71]([CH2:87][C:88]([OH:90])=[O:89])=[CH:72][CH:73]=1

Participants

5

Reactant 2

HCID 86753148HCID 86753148, compoundHCID 86753149HCID 86753149, compound

Product 1

HCID 14801625HCID 14801625, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

100 mg of benzyl 5-[(N-benzyloxycarbonyl-L-valyl-L-alanyl-L-alanyl-L-phenylalanyl-L-leucyl-L-alanyl-L-leucyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate (benzyl 5-[(N-benzyloxycarbonyl-SEQ ID NO:9)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate) were dissolved in 200 ml of hexafluoroisopropanol, treated with 60 mg of palladium on calcium carbonate (10%) and stirred under hydrogen for 3 hours. After filtering the catalyst the filtrate was concentrated. The residue remaining was washed several times with methanol and thereafter chromatographed over silica gel in chloroform/methanol/hexafluoroisopropanol, whereby 65 mg of 3,6-dimethoxy-9,9-dimethyl-5-[(L-valyl-L-alanyl-L-alanyl-L-phenylalanyl-L-leucyl-L-alanyl-L-leucyl-L-alanyl)aminomethyl]xanthene-4-acetic acid (3,6-dimethoxy-9,9-dimethyl-5-[(SEQ ID NO:9)aminomethyl]xanthene-4-acetic acid) were obtained; IR 3393, 3288, 2963, 1685, 1636, 1531 cm-1.

Workup

  1. filtrationAfter filtering the catalyst the filtrate
  2. concentrationwas concentrated
  3. washThe residue remaining was washed several times with methanol
  4. customchromatographed over silica gel in chloroform/methanol/hexafluoroisopropanol, whereby 65 mg of 3,6-dimethoxy-9,9-dimethyl-5-[(L-valyl-L-alanyl-L-alanyl-L-phenylalanyl-L-leucyl-L-alanyl-L-leucyl-L-alanyl)aminomethyl]xanthene-4-acetic acid (3,6-dimethoxy-9,9-dimethyl-5-[(SEQ ID NO

Sources & evidence

ORD record
ord-fafade14265347488b6060d035d8a834
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

Loading…