Water → HCID 70027409, compound

HRID 1058452Notes

Reaction equation

HRID 1058452 reaction equation
[CH3:1]N(C)C(N(C)C)=N.[CH3:9][O:10][C:11](=[O:43])[CH:12](P(OC)(OC)=O)[NH:13][C:14](=[O:36])[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]([O:31][CH2:32][O:33][CH3:34])[CH:26]=2)=[O:22])=[CH:17][C:16]=1[Cl:35].C([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[S:52]([NH2:55])(=[O:54])=[O:53])=O.O>COCCOC>[CH3:9][O:10][C:11](=[O:43])/[C:12](/[NH:13][C:14](=[O:36])[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]([O:31][CH2:32][O:33][CH3:34])[CH:26]=2)=[O:22])=[CH:17][C:16]=1[Cl:35])=[CH:1]/[C:50]1[CH:51]=[CH:46][C:47]([S:52]([NH2:55])(=[O:53])=[O:54])=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 962WaterHCID 664601,1,3,3-TetramethylguanidineHCID 186730142-FormylbenzenesulfonamideHCID 23560760HCID 23560760, compound

Product 1

HCID 70027409HCID 70027409, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1,1,3,3-Tetramethylguanidine (0.046 g, 0.40 mmol) was added to a solution of rac.-N-[2-chloro-4-[[(3-methoxymethoxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 142; 0.047 g, 0.10 mmol) and 4-15 formylbenzenesulfonamide (lit.: Van Es, T.; Staskun, B. Organic Syntheses 1971, 51, 20-23; 0.019 g, 0.10 mmol) in DME (4 mL). The solution was stirred at room temperature for 20 h and then was poured into water (25 mL). The aqueous layer was extracted with ethyl acetate and the organic layers were dried (Na2SO4), filtered and evaporated to give crude (Z)-3-(4-aminosulfonylphenyl)-2-[[2-chloro-4-[[(3-methoxymethoxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester. A solution of tetrahydrofuran/methanol/water (3:1:1; 4 mL) was added, followed by lithium hydroxide monohydrate (7 mg, 0.17 mmol). The mixture was stirred at room temperature for 24 h, neutralized with 1N hydrochloric acid solution and extracted with ethyl acetate.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialthe organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-6df8a0f1061947239fc0784c40853a0a
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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