1,1,3,3-Tetramethylguanidine → HCID 59038473, compound

HRID 1058432Notes

Reaction equation

HRID 1058432 reaction equation
CN(C)C(N(C)C)=N.[CH3:9][O:10][C:11](=[O:40])[CH:12](P(OC)(OC)=O)[NH:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][C:18]([CH:21]([OH:31])/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)=[CH:17][C:16]=1[Cl:32].[N:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[C:43]([CH:51]=O)[CH:42]=1>O1CCCC1>[CH3:9][O:10][C:11](=[O:40])/[C:12](/[NH:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][C:18]([CH:21]([OH:31])/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)=[CH:17][C:16]=1[Cl:32])=[CH:51]/[C:43]1[CH:42]=[N:41][C:50]2[C:45]([CH:44]=1)=[CH:46][CH:47]=[CH:48][CH:49]=2

Participants

5

Reactant 3

HCID 664601,1,3,3-TetramethylguanidineHCID 836413-QuinolinecarboxaldehydeHCID 23560741HCID 23560741, compound

Product 1

HCID 59038473HCID 59038473, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1,3,3-Tetramethylguanidine (60 μL, 0.48 mmol) was added to a solution of rac.-(E)-N-[2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 135; 116 mg, 0.24 mmol) in tetrahydrofuran (5 mL) at −20° C. After 10 min, quinoline-3-carboxaldehyde (40 mg, 0.255 mmol) was added and the solution was stirred at room temperature for 16 h. After the solvent was removed in vacuo, the residue was taken up in ethyl acetate (10 mL) and the solution was washed with saturated sodium bicarbonate solution (10 mL) and brine (10 mL). Each aqueous layer was back-extracted with ethyl acetate (10 mL). The combined organic extracts were dried, filtered, evaporated and chromatographed (50% ethyl acetate/hexanes) to give rac.-(Z)-2-[[2-chloro-4-[(E)-1-hydroxy-3-(3-hydroxyphenyl)prop-2-en-1-yl]benzoyl]amino]-3-(quinolin-3-yl)propenoic acid methyl ester (110 mg, 89% yield) as a colorless solid.

Workup

  1. customAfter the solvent was removed in vacuo
  2. washthe solution was washed with saturated sodium bicarbonate solution (10 mL) and brine (10 mL)
  3. extractionEach aqueous layer was back-extracted with ethyl acetate (10 mL)
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3252932815714cc790afd3c174a27c99
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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