Benzaldehyde → HCID 59918713, compound

HRID 1058424Notes

Reaction equation

HRID 1058424 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[CH3:32].[CH:41](=O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>ClCCl>[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[CH3:32])=[CH:41]/[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 664601,1,3,3-TetramethylguanidineHCID 23560783HCID 23560783, compound

Product 1

HCID 59918713HCID 59918713, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,1,3,3-Tetramethylguanidine (0.20 g, 1.7 inmol) was added to a solution of rac.-N-[4-[[(3-hydroxybenzyl)anlino]carbonyl]-2-methylbenzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 140; 0.40 g, 0.9 mmol) and benzaldehyde (0.10 g, 0.9 mmol) in dichloromethane (50 mL) at room temperature and the reaction was stirred at ambient temperature over the weekend. The solution was diluted with dichloromethane (200 mL) and washed in turn with 1N hydrochloric acid solution, water and brine (200 mL each), dried (MgSO4) and evaporated to give (Z)-2-[[4-[[(3-hydroxybenzyl)amino]carbonyl]-2-methylbenzoyl]amino]-3-phenylpropenoic acid methyl ester (300 mg, 78% yield) which was used directly in a subsequent step.

Workup

  1. washwashed in turn with 1N hydrochloric acid solution, water and brine (200 mL each)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-64805dba7fa14b409e22b3058058aa58
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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