Sodium Hydroxide → HCID 56926729, compound

HRID 595346Notes

Reaction equation

HRID 595346 reaction equation
[C:1]1([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:13]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1>[C:31]1([CH2:30][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][C@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:13]=2)[OH:11])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67451092HCID 67451092, compound

Product 1

HCID 56926729HCID 56926729, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[bis(phenylmethyl)amino]-1-[3-({3[(phenylmethyl)oxy]propyl}oxy)phenyl]-ethanone, catalyst SK-N003-2z (Naud catalyst, 47 mg) and 1M sodium hydroxide (2.085 mL) in tetrahydrofuran (10 mL) was set under hydrogen at 150 psi for 4 h. The reaction mixture was then filtered through silica gel. The crude filtrate was purified by chromatography eluting with tert-butyl methyl ether-hexane (0-60%) to yield the desired product as a yellow oil.

Workup

  1. filtrationThe reaction mixture was then filtered through silica gel
  2. customThe crude filtrate was purified by chromatography
  3. washeluting with tert-butyl methyl ether-hexane (0-60%)

Sources & evidence

ORD record
ord-a96aa34c8d2f44f2834cf61decbf2466
Source dataset
uspto-grants-2016_01
Patent number
US09243003B2

Reaction notes

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