Hydrochloric Acid → (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester

HRID 1058427Notes

Reaction equation

HRID 1058427 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]=1Cl.[Br:41][C:42]1[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=1.[ClH:50]>O1CCCC1.O1CCOCC1>[CH3:9][O:10][C:11](=[O:40])/[C:12](/[NH:13][C:14](=[O:33])[C:15]1[CH:16]=[CH:17][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:19][C:20]=1[Cl:50])=[CH:46]/[C:45]1[CH:48]=[CH:49][C:42]([Br:41])=[CH:43][CH:44]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 664601,1,3,3-TetramethylguanidineHCID 707414-BromobenzaldehydeHCID 23560750HCID 23560750, compound

Product 1

HCID 59038409(Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl esterYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1,3,3-Tetramethylguanidine (0.047 g, 0.41 mmol) was added to a solution of rac.-N-[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 141; 0.10 g, 0.21 mmol) and 4-bromobenzaldehyde (0.076 g, 0.412 mmol) in tetrahydrofuran (1.5 mL). Dioxane (1.5 mL) was added to bring everything into solution and the reaction mixture was stirred at room temperature for 15 h. The solution was then poured into 1N hydrochloric acid solution and the aqueous phase was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residual material was chromatographed over silica gel (45% ethyl acetate/hexanes) to give (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester (69 mg, 62% yield).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residual material was chromatographed over silica gel (45% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8fa00c8d5dd44fd08da5f7d45474c37c
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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