Diethylethanolamine → Methyl 3-[2-(2-diethylaminoethoxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate

HRID 250924Notes

Reaction equation

HRID 250924 reaction equation
[CH2:1]([NH:8][C:9](=[O:31])[N:10]([C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][C:19]=2[OH:30])[CH:15]=[CH:16][CH:17]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:32]([N:34]([CH2:38][CH3:39])[CH2:35][CH2:36]O)[CH3:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:32]([N:34]([CH2:38][CH3:39])[CH2:35][CH2:36][O:30][C:19]1[CH:20]=[C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:22]=[CH:23][C:18]=1[C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([N:10]([CH3:11])[C:9]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:31])[CH:13]=1)[CH3:33]

Participants

6

Reactant 4

HCID 7497DiethylethanolamineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11582687Methyl 3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate

Product 1

HCID 67272954Methyl 3-[2-(2-diethylaminoethoxy)-3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 500 mg (1.17 mmol, 1 eq) of methyl 3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate (prepared in Example 15f) in 5 ml of tetrahydrofuran in the presence of 150 mg (1.29 mmol, 1.1 eq) of 2-diethylaminoethanol, 460 mg (1.76 mmol, 1.5 eq) of triphenylphosphine and 280 μL (1.76 mmol, 1.5 eq) of diethyl azodicarboxylate (DEAD) is stirred at room temperature for 24 hours. The reaction medium is concentrated and the residue is then chromatographed on silica gel (40/60 heptane/ethyl acetate). 490 mg of methyl 3-[2-(2-diethylaminoethoxy)-3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propanoate are obtained. Yield=80%

Workup

  1. concentrationThe reaction medium is concentrated
  2. customthe residue is then chromatographed on silica gel (40/60 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-334cb10738784482b9a400eb0ac3fb32
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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