Tributylphosphine → HCID 66648457, compound

HRID 1774412Notes

Reaction equation

HRID 1774412 reaction equation
[CH3:1][O:2][C:3](=[O:21])/[C:4](/[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[C:5](/[CH:10]([CH3:12])[CH3:11])\[C:6]([O:8][CH3:9])=[O:7].[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31]O)=[O:28])([CH3:25])([CH3:24])[CH3:23].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1C=CC=CC=1>[C:22]([O:26][C:27]([NH:29][CH2:30][CH2:31][O:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13]/[C:4](=[C:5](\[CH:10]([CH3:11])[CH3:12])/[C:6]([O:8][CH3:9])=[O:7])/[C:3]([O:2][CH3:1])=[O:21])=[CH:19][CH:18]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 59706557HCID 59706557, compound

Product 1

HCID 66648457HCID 66648457, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2-(4-hydroxybenzyl)-3-isopropylmaleic acid dimethyl ester (204.5 mg, 0.6996 mmol) in benzene (6 mL) were added N-(t-butoxycarbonyl)ethanolamine (343 mg, 2.13 mol), tributylphosphine (853 mg, 4.20 mmol) and 1,1′-(azodicarbonyl)dipiperidine (1.05 g, 4.20 mmol) with stirring at room temperature. After stirring at room temperature for 1 h, the reaction mixture was filtered, and the residue obtained by concentrating the filtrate under reduced pressure was subjected to silica gel column chromatography (hexane-ethyl acetate 2:1) to give 287 mg of dimethyl 2-{4-[2-(t-butoxycarbonylamino)ethoxy]benzyl}-3-isopropylmaleate as oil (yield: 98%).

Workup

  1. stirringAfter stirring at room temperature for 1 h
  2. filtrationthe reaction mixture was filtered
  3. customthe residue obtained
  4. concentrationby concentrating the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c5420720e2c04db99c0f33b58ccd9d26
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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