HCID 69691598, compound → HCID 69692657, compound

HRID 1814390Notes

Reaction equation

HRID 1814390 reaction equation
[C:1]([O:5][C:6](=[O:43])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[O:28])=[CH:22][C:21]=1[O:35]CC1C=CC=CC=1)(=[O:19])=[O:18])[CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:43])[CH2:7][C@H:8]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([NH:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[O:28])=[CH:22][C:21]=1[OH:35])(=[O:18])=[O:19])[CH:9]([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 69691598HCID 69691598, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69692657HCID 69692657, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To (S)-3-{2-benzyloxy-4-[3-(2-dimethylamino-ethyl)-ureido]-benzenesulfonylamino}-4,4-diethoxy-butyric acid tert-butyl ester (1.80 g, 2.9 mmol) in ethanol (100 mL) was added 20% Pd on carbon (250 mg) and stirred under 1 atmosphere of hydrogen for 24 h. The reaction was judged complete by thin layer analysis and filtered. The filtrate was evaporated to give (S)-3-{4-[3-(2-dimethylamino-ethyl)-ureido]-2-hydroxy-benzenesulfonylamino}-4,4-diethoxy-butyric acid tert-butyl ester as a colorless foam 1.54 g (100%). MS (APCI) m/z 533.4 (M+1).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-fe440a4b0d634d5ea95706ea98a3445d
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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