Triphenylphosphine → 2-Methyl-2-{[1-(3-phenyl-butoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester

HRID 1889260Notes

Reaction equation

HRID 1889260 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[OH:20])=[O:9])([CH3:6])[CH3:5].[C:22]1([CH:28]([CH3:32])[CH2:29][CH2:30]O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:6])([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:30][CH2:29][CH:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:32])=[O:9])[CH3:5]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 94243Benzenepropanol, gamma-methyl-HCID 5363146Diisopropyl azodicarboxylate2×HCID 667009722-[(1-Hydroxy-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester

Product 1

HCID 688424952-Methyl-2-{[1-(3-phenyl-butoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. to a solution of 80 mg of 2-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester, 42 mg 3-phenyl-1-butanol and 73 mg triphenyl phosphine in 3 ml of dry THF 56 mg of diisopropylazodicarboxylate were added. After 2 h and again after 4 h at room temperature 36 mg of triphenylphosphine and 25 mg of diisopropylazodicarboxylate were added. After additional 12 h the reaction was concentrated in vacuo and after chromatography on silica (ethyl acetate/heptane) 110 mg of 2-methyl-2-{[1-(3-phenyl-butoxy)-naphthalene-2-carbonyl]-amino}-propionic acid methyl ester were obtained.

Workup

  1. concentrationAfter additional 12 h the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-c4a2eaa2e4964e3b8ed342f15eca4613
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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