Z-Phe-Val-N-Me-Tyr(3-tBu)-NH2 → (S)-N-((S)-1-amino-3-(3-tert-butyl-4-hydroxyphenyl)-1-oxopropan-2-yl)-2-((S)-2-amino-3-phenylpropanamido)-N,3-dimethylbutanamide

HRID 1383723Notes

Reaction equation

HRID 1383723 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([NH:12][C@H:13]([C:17]([N:19]([CH3:36])[C@H:20]([C:33]([NH2:35])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>CO.[C].[Pd]>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:17]([N:19]([CH3:36])[C@H:20]([C:33]([NH2:35])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([CH3:30])([CH3:32])[CH3:31])[CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 131722739Z-Phe-Val-N-Me-Tyr(3-tBu)-NH2HCID 178418361HCID 178418361, compound

Product 1

HCID 44583347(S)-N-((S)-1-amino-3-(3-tert-butyl-4-hydroxyphenyl)-1-oxopropan-2-yl)-2-((S)-2-amino-3-phenylpropanamido)-N,3-dimethylbutanamide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 183 mg (0.290 mmol) of Z-Phe-Val-N-Me-Tyr(3-tBu)-NH2 in 3 ml of methanol, 100 mg of 10% palladium carbon was added and the mixture was stirred in a hydrogen atmosphere at room temperature for 5 hours. After filtering, the filtrate was concentrated under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:methanol=10:1) to yield Phe-Val-N-Me-Tyr(3-tBu)-NH2 in the amount of 108 mg (75%). NMR(method g,CDCl3): δ 0.69(3H,dd,J=6.9,17.8 Hz), 0.89(3H,dd,J=6.9,14.5 Hz), 1.36(9/2H,s), 1.39(9/2H,s), 2.67(1H,dd,J=9.6,13.5 Hz), 2.78-2.94(1H,m), 2.97(3/2H,s), 3.09(3/2H,s), 3.12-3.40(2H,m), 3.59(1H,ddd,J=3.6,9.3,10.2 Hz), 4.34-4.42(1/2H,m), 4.68(1/2H,dd,J=6.6,11.1 Hz), 4.79(1/2H,dd,J=7.9,8.9 Hz), 5.18-5.26(1/2H,m), 5.35(1/2H,brs), 5.49(1/2H,brs), 6.60(1H,dd,J=7.9,12.2 Hz), 6.86(1H,ddd,J=1.6,6.3,6.3 Hz), 7.06(1H,s), 7.16-7.34(5H,m), 7.76(1/2H,brs), 7.85(1/2H,d,J=8.9 Hz), 7.95(1/2H,d,J=7.9 Hz).

Workup

  1. filtrationAfter filtering
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-054ed3cb6727491dbb105a30ef6bb663
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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