Ethyl Acetate → (R)-tert-butyl (6-(4-(4-aminophenyl)butoxy)hexyl)(2-(2,8-bis((tert-butoxycarbonyl)oxy)quinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)carbamate

HRID 385272Notes

Reaction equation

HRID 385272 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[C:12]([O:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH:13]=[CH:14][C:15]=2[C@@H:19]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[CH2:20][N:21]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-])=O)=[CH:42][CH:41]=2)[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.[H][H]>CO.[Pd]>[NH2:46][C:43]1[CH:44]=[CH:45][C:40]([CH2:39][CH2:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][N:21]([CH2:20][C@@H:19]([C:15]2[CH:14]=[CH:13][C:12]([O:57][C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])=[C:11]3[C:16]=2[CH:17]=[CH:18][C:9]([O:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:10]3)[O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:51])[CH3:52])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 58505287(R)-tert-butyl (2-(2,8-bis((tert-butoxycarbonyl)oxy)quinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)(6-(4-(4-nitrophenyl)butoxy)hexyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 66989909(R)-tert-butyl (6-(4-(4-aminophenyl)butoxy)hexyl)(2-(2,8-bis((tert-butoxycarbonyl)oxy)quinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Intermediate 41 (175 mg, 0.19 mmol) was dissolved in methanol (4 mL) and ethyl acetate (1 mL) and treated with palladium on carbon (10% w/w, wet Degussa-type, catalytic amount). The suspension was stirred under a balloon of hydrogen gas for 45 minutes. The mixture was then filtered through a pad of Celite diatomaceous earth, and the filtrate was concentrated to dryness under reduced pressure to provide the title material. ES/MS calcd. for C48H76N3O10Si+882.5. found m/z=882.5 (M+H)+.

Workup

  1. filtrationThe mixture was then filtered through a pad of Celite diatomaceous earth
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6381dd4d6abc4a449ed755e45c0b19bb
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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