Trimethyl phosphonoacetate → HCID 69373271, compound

HRID 860989Notes

Reaction equation

HRID 860989 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=O)[CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].C[O:33][C:34](=[O:42])[CH2:35]P(OC)(OC)=O.CC([O-])(C)C.[K+]>C1COCC1>[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:19]=[C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]=[CH:35][C:34]([OH:42])=[O:33])[CH:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:6])[CH3:7])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 80029Trimethyl phosphonoacetateHCID 10071304HCID 10071304, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 69373271HCID 69373271, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3′-[6-(1-methanesulfonyl-1-methyl-ethyl)quinolin-8-yl]-biphenyl-3-carbaldehyde from Step 1 (1.0 eq.) and (dimethoxy-phosphoryl)-acetic acid methyl ester (1.1 eq.) in THF (0.1M) was added t-BuOK (1.1 eq.; 1.0M in THF). The final mixture was stirred 3 h at rt, poured in saturated aqueous NH4 Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (CH2Cl2:EtOAc; 9:1) afforded the corresponding methyl ester of the title compound as a yellow solid. To a solution of the methyl ester in THF: MeOH (4:1), aqueous NaOH (3.0 eq.) was added. The final mixture was stirred 4 h at rt, neutralized with AcOH, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64789d4554f7484c8928303cf31fb1c7
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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