Methyl chloroacetate → HCID 86745784, compound
Reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].Cl[CH2:12][C:13]([O:15][CH3:16])=[O:14].C[O-:18].[Na+].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[SH:27]>CO.C1(C)C=CC=CC=1>[OH:18][CH:12]([CH:7]([S:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH2:20])[C:6]1[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:13]([O:15][CH3:16])=[O:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A cyano glycidic acid ester compound can be prepared by reaction of an alkyl haloester and a cyano-aldehyde in the presence of an alkali metal alkoxide; an amino-acid ester cyano compound can be prepared by reaction of the cyano glycidic acid ester compound and an attachable amino compound, and a cyclic amido-carbonyl cyano compound can be prepared by contact of the amino-acid ester cyano compound in a liquid medium with a heterogeneous acidic ion-exchange substance. For example, reaction of 4-cyanobenzaldehyde and methyl chloroacetate in the presence of sodium methoxide in methanol, followed by ice/acetic acid neutralization, prepares trans-3-(4-cyanophenyl)glycidic acid, methyl ester, which is reacted in toluene with 2-aminothiophenol to yield 2-hydroxy-3-(2-aminophenylthio)-3-(4-cyanophenyl)propionic acid, methyl ester, threo form, which is cyclized in an aqueous mixture into cis-2-(4-cyanophenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one by employing a sulfonated polystyrenedivinylbenzene ion-exchange resin in its acid form, e.g., Dowex 50X4-400, at cyclization yields exceeding 70 percent of theory. Compounds of this invention are useful pharmaceuticals.
Sources & evidence
- ORD record
- ord-1fe1fe45dfed4cf4975d63b6c3766ae3
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05112969
Reaction notes
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