2-Naphthalenecarboxaldehyde → (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(naphthalen-2-yl)propenoic acid methyl ester

HRID 1058416Notes

Reaction equation

HRID 1058416 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]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:17][C:16]=1[Br:32].[CH:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][C:42]=1[CH:51]=O.C(OCC)(=O)C>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]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:17][C:16]=1[Br:32])=[CH:51]/[C:42]1[CH:43]=[CH:44][C:45]2[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:41]=1

Participants

6

Reactant 4

HCID 62012-NaphthalenecarboxaldehydeHCID 8857Ethyl AcetateHCID 664601,1,3,3-TetramethylguanidineHCID 23560709Rac.-n-[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester

Product 1

HCID 59038424(Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(naphthalen-2-yl)propenoic acid methyl esterYield 78.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

1,1,3,3-Tetramethylguanidine (50.5 μL, 0.40 mmol) was added to a solution of rac.-N-[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 130; 106.4 mg, 0.20 mmol) in tetrahydrofuran (1 mL) at −20° C. After 5 min, a solution of naphthalene-2-carboxaldehyde (31.4 mg, 0.20 mmol) in tetrahydrofuran (0.5 mL) was added. The solution was stirred at −20° C. for 1 h and then was stirred at room temperature for 4 h. Ethyl acetate (15 mL) was added and the solution was washed with 1N hydrochloric acid solution (10 mL) and brine (10 mL). The dried (MgSO4) organic phase was filtered, evaporated and the resulting residue was triturated with petroleum ether to furnish (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(naphthalen-2-yl)propenoic acid methyl ester (88 mg, 78% yield) as a yellow solid.

Workup

  1. stirringwas stirred at room temperature for 4 h
  2. washthe solution was washed with 1N hydrochloric acid solution (10 mL) and brine (10 mL)
  3. dry with materialThe dried (MgSO4) organic phase
  4. filtrationwas filtered
  5. customevaporated
  6. customthe resulting residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-0cad13dda78343c9a5ec91b267cb464c
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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