4-Benzyl 1,4-di-tert-butyl (1S)-5-[5-(benzyloxy)pyridin-2-yl]-1-[(tert-butoxycarbonyl)amino]pentane-1,4,4-tricarboxylate → (5S)-6-tert-Butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[(5-hydroxypyridin-2-yl)methyl]-6-oxohexanoic acid

HRID 591304Notes

Reaction equation

HRID 591304 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])([C:35]([O:37]CC2C=CC=CC=2)=[O:36])[CH2:17][CH2:18][C@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:23]([O:22][C:20](=[O:21])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:18][CH2:17][C:16]([C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])([CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][N:13]=1)[C:35]([OH:37])=[O:36])([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 1178126974-Benzyl 1,4-di-tert-butyl (1S)-5-[5-(benzyloxy)pyridin-2-yl]-1-[(tert-butoxycarbonyl)amino]pentane-1,4,4-tricarboxylate

Product 1

HCID 70977774(5S)-6-tert-Butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[(5-hydroxypyridin-2-yl)methyl]-6-oxohexanoic acidYield 101.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 310 mg of 4-benzyl 1,4-di-tert-butyl (1S)-5-[5-(benzyloxy)pyridin-2-yl]-1-[(tert-butoxycarbonyl)amino]pentane-1,4,4-tricarboxylate (0.44 mmol) in methanol (10 mL) was added a 10% palladium on carbon hydrogenation catalyst (15 mg) at room temperature. The suspension was stirred for 3 h at room temperature under an atmosphere of hydrogen. The catalyst was removed by filtration and all volatiles were removed in vacuo. The crude product (234 mg, quantitative yield) was used in the next step without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. customall volatiles were removed in vacuo

Sources & evidence

ORD record
ord-9460234fbd744e6baab04d5f9cade836
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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