di-tert-butyl (5R)-2-[4-(benzyloxy)benzyl]-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate → HCID 70941355, compound

HRID 591279Notes

Reaction equation

HRID 591279 reaction equation
C([O:8][C:9]1[CH:51]=[CH:50][C:12]([CH2:13][C:14]([C:40]([O:42]CC2C=CC=CC=2)=[O:41])([CH2:22][CH2:23][C@@H:24]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[C:28]([O:27][C:25](=[O:26])[C@H:24]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:23][CH2:22][C:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])([CH2:13][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:51][CH:50]=1)[C:40]([OH:42])=[O:41])([CH3:29])([CH3:30])[CH3:31]

Participants

4

Reactant 1

HCID 117812692di-tert-butyl (5R)-2-[4-(benzyloxy)benzyl]-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate

Product 1

HCID 70941355HCID 70941355, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 370 mg di-tert-butyl (5R)-2-[4-(benzyloxy)benzyl]-2-(benzyloxycarbonyl)-5-[(tert-butoxycarbonyl)amino]hexanedioate (0.53 mmol) in methanol (10 mL) was added a 10% palladium on carbon hydrogenation catalyst (50 mg) at room temperature. The suspension was stirred for 2.5 hours at room temperature under an atmosphere of hydrogen. The catalyst was removed by filtration and all volatiles were removed in vacuo. The crude product (273 mg, 99% 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-7451003742ca47fcae978249738cfdef
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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