HCID 89939678, compound → HCID 68310377, compound

HRID 922424Notes

Reaction equation

HRID 922424 reaction equation
C(OC([NH:11][CH2:12][C:13]#[C:14][C:15]1[CH:16]=[C:17]([CH:23]([N:25]([CH:41]2[CH2:43][CH2:42]2)[C:26]([C@@H:28]2[O:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]2)=[O:27])[CH3:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:23]([N:25]([CH:41]2[CH2:43][CH2:42]2)[C:26]([C@@H:28]2[O:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:29]2)=[O:27])[CH3:24])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]

Participants

4

Reactant 1

HCID 89939678HCID 89939678, compound

Product 1

HCID 68310377HCID 68310377, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

to a solution of tert-butyl (2R)-2-{[{1-[3-(3-{[(benzyloxy)carbonyl]amino}prop-1-yn-1-yl)-4-methoxyphenyl]ethyl}(cyclopropyl)amino]carbonyl}morpholin-4-carboxylate (2.82 g) in methanol (25 mL) was added 10% palladium on carbon (282 mg), and the mixture was stirred under hydrogen for 7 hours. An insoluble was filtered off, and then the filtrate was concentrated under reduced pressure, and the resulting residue was purified by NH-silica gel column chromatography (eluent: chloroform→chloroform/methanol=33/1) to give tert-butyl (2R)-2-{[{1-[3-(3-aminopropyl)-4-methoxyphenyl]ethyl}(cyclopropyl)amino]carbonyl}morpholin-4-carboxylate [Ex(295-4)] (1.49 g) as a colorless oil.

Workup

  1. filtrationAn insoluble was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by NH-silica gel column chromatography (eluent: chloroform→chloroform/methanol=33/1)

Sources & evidence

ORD record
ord-e3f0e156207d43dab627779c8bb83bd1
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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