HCID 131721153, compound → HCID 131721152, compound

HRID 1418108Notes

Reaction equation

HRID 1418108 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@@H:2]([C:10]([NH:12][C@@H:13]([C:26]([O:28][CH3:29])=[O:27])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=1)=[O:11])[C@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[H][H]>[Pd]>[NH2:1][C@@H:2]([C:10]([NH:12][C@@H:13]([C:26]([O:28][CH3:29])=[O:27])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=1)=[O:11])[C@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 131721153HCID 131721153, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131721152HCID 131721152, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4.03 g of Z-D-Thr(tBu)-D-Tyr(tBu)-OMe (7.45 mmoles) were dissolved in 250 ml of CH30H. After addition of 850 mg of 10% Pd on activated charcoal (Fluka, cat. No 75990) a hydrogen stream was blown on the solution at room temperature under shaking for 4 h. The hydrogenation reaction was monitored by TLC. After removal of the catalyst by filtration and evaporation of the filtrate, 2.88 g (7.08 mmoles, yield 95%) of H-D-Thr(tBu)-D-Tyr(tBu)-OMe were obtained in the form of pure oil (TLC).

Workup

  1. customwas blown on the solution at room temperature
  2. customThe hydrogenation reaction
  3. customAfter removal of the catalyst
  4. filtrationby filtration and evaporation of the filtrate

Sources & evidence

ORD record
ord-52194e4a6a354243afea309bf206d57d
Source dataset
uspto-grants-1999_03
Patent number
US05880259

Reaction notes

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