HCID 13393252, compound → HCID 13606280, compound
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][CH:12]([NH2:16])[C:13]([OH:15])=[O:14])[C:3]1=[O:17].[Cl:18][C:19]1[CH:36]=[CH:35][C:22]([C:23](N2C3C=CC=CC=3OC2=S)=[O:24])=[CH:21][CH:20]=1>CN1CCCC1=O>[Cl:18][C:19]1[CH:36]=[CH:35][C:22]([C:23]([NH:16][CH:12]([CH2:11][CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[C:3]2=[O:17])[C:13]([OH:15])=[O:14])=[O:24])=[CH:21][CH:20]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2 Grams of 3-(1-methyloxindol-3-yl)-2-aminopropionic acid prepared in Reference Example 5 was suspended in 50 ml of 1-methyl-2-pyrrolidone, then 2.2 g of 3-(4-chlorobenzoyl)benzoxazolin-2-thione was added thereto, and the reaction mixture was stirred at a room temperature for 3 days. The reaction mixture was poured into an ice-water, and the crystals formed were collected by filtration, then the crystals were dissolved in 1N-sodium hydroxide aqueous solution, then the resulting solution was acidified by using 10%-hydrochloric acid, and the crystals formed were collected by filtration. The crystals were dried, washed with chloroform, there was obtained 1.1 g of 2-(4-chlorobenzoylamino)-3-(1-methyloxindol-3-yl)propionic acid. White powdery substance. Melting point: 115°-120° C.
Workup
- customthe crystals formed
- filtrationwere collected by filtration
- dissolutionthe crystals were dissolved in 1N-sodium hydroxide aqueous solution
- customthe crystals formed
- filtrationwere collected by filtration
- customThe crystals were dried
- washwashed with chloroform
Sources & evidence
- ORD record
- ord-1ed9042cf3194b47b11b99730c287ff6
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04694017
Reaction notes
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