Z-Tyr(3-tBu)-NH2 → Tyr(3-tBu)-NH2

HRID 1383715Notes

Reaction equation

HRID 1383715 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:15]([NH2:17])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[H][H]>CO.[C].[Pd]>[NH2:1][C@H:2]([C:15]([NH2:17])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:12])[CH3:13])[CH:5]=1

Participants

5

Reactant 2

HCID 131722728Z-Tyr(3-tBu)-NH2HCID 178418361HCID 178418361, compound

Product 1

HCID 131722727Tyr(3-tBu)-NH2

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 9.89 g (26.7 mmol) of Z-Tyr(3-tBu)-NH2 in 350 ml of methanol, 3.5 g of 10% palladium carbon was added and the mixture was stirred in a hydrogen atmosphere at room temperature for 10 hours. After filtering, the filtrate was concentrated under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluting solvent; methylene chloride:methanol=20:1) to yield Tyr(3-tBu)-NH2 in the amount of 5.11 g (81%). NMR(method g,CDCl3): δ 1.40(9H,s), 2.64(1H,dd,J=9.6,13.9 Hz), 3.18(1H,dd,J=4.0,13.9 Hz), 3.49(1H,s), 3.58(1H,dd,J=4.0,9.6 Hz), 5.45(1H,brs), 6.65(1H,d,J=7.9 Hz), 6.92(1H,dd,J=2.0,12.0 Hz), 7.10(1H,d,J=2.0 Hz), 6.94(1H,d,6.6 Hz), 7.2-7.4(8H,m), 7.7-7.9(2H,m), 8.46(1H,d,7.6 Hz), 9.06(1H,d).

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; methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-bb176c22b59f4753b18c7e5e6286328c
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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