HCID 86758137, compound → HCID 10166762, compound

HRID 2185945Notes

Reaction equation

HRID 2185945 reaction equation
[C:1]1([S:7]([C:10]2([C:16]([NH:18][C@H:19]([C:45]([OH:47])=[O:46])[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[C:32]([O:33][CH3:34])=[CH:31][CH:30]=[CH:29][C:28]=4[O:35][CH3:36])=[CH:23][C:22]=3[O:37]CC3C=CC=CC=3)=[O:17])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd]>[C:1]1([S:7]([C:10]2([C:16]([NH:18][C@H:19]([C:45]([OH:47])=[O:46])[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[C:28]([O:35][CH3:36])=[CH:29][CH:30]=[CH:31][C:32]=4[O:33][CH3:34])=[CH:23][C:22]=3[OH:37])=[O:17])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 86758137HCID 86758137, compound

Product 1

HCID 10166762HCID 10166762, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of N-(3-phenylsulfonyl-nipecotyl)-4-(2′,6′-dimethoxyphenyl)-2-benzyloxyphenylalanine (36 mg, 0.055 mmol) and 10% Pd/C (10 mg) were stirred vigorously under 1 atm of H2 until the starting material was consumed as judged by reverse phase HPLC analysis. The mixture was filtered through a pad of celite which was washed with MeOH and concentrated. The filtrate was triturated with Et2O to afford N-(3-phenylsulfonyl-nipecotyl)-4-(2′,6′-dimethoxyphenyl)-2-hydroxyphenylalanine as a solid.

Workup

  1. customwas consumed
  2. filtrationThe mixture was filtered through a pad of celite which
  3. washwas washed with MeOH
  4. concentrationconcentrated
  5. customThe filtrate was triturated with Et2O

Sources & evidence

ORD record
ord-a83219cef7b44be18d0fc8eb916620bf
Source dataset
uspto-grants-2002_06
Patent number
US06403584B1

Reaction notes

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