Benzamidine → HCID 178498279, compound

HRID 234243Notes

Reaction equation

HRID 234243 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[C:6]([O:13][Si:14]([CH3:22])([CH3:21])[C:15]([CH3:20])([CH3:19])[CH:16]([CH3:18])[CH3:17])[C:5]=1[CH2:23][S:24][CH2:25][C@H:26]([NH2:33])[C:27]1[O:31][N:30]=[C:29]([CH3:32])[N:28]=1.[C:35](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:36].[C:51]([NH2:59])(=[NH:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>ClCCl>[CH3:1][O:2][C:3](=[O:34])[C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[C:6]([O:13][Si:14]([CH3:21])([CH3:22])[C:15]([CH3:19])([CH3:20])[CH:16]([CH3:17])[CH3:18])[C:5]=1[CH2:23][S:24][CH2:25][C@H:26]([NH:33][C:35]([NH:58][C:51](=[NH:59])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[S:36])[C:27]1[O:31][N:30]=[C:29]([CH3:32])[N:28]=1

Participants

5

Reactant 3

HCID 2332BenzamidineHCID 8531621,1'-Thiocarbonyldi-2(1H)-pyridoneHCID 53739152(R)-2-[2-amino-2-(3-methyl-1,2,4-oxadiazol-5-yl)-ethylsulfanyl-methyl]-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methoxy-6-methyl-benzoic acid methyl ester

Product 1

HCID 178498279HCID 178498279, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 400 mg of (R)-2-[2-amino-2-(3-methyl-1,2,4-oxadiazol-5-yl)-ethylsulfanyl-methyl]-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-methoxy-6-methyl-benzoic acid methyl ester in 20 ml of dry dichloromethane were added slowly 186 mg of 1,1'-thiocarbonyldi-2(1H)-pyridone. The red solution was stirred for 30 min at room temperature and then cooled in an ice bath. Upon the addition of 94 mg of benzamidine (~85%), stirring was continued for 1 h at 0° C. and for 10 h at 20° C. . The solution was evaporated in vacuo and the residue was chromatographed on silica gel using ethyl acetate/hexane (2:1, v/v) as eluent to afford 480 mg of (R)-3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-[2-[3-(iminophenyl-methyl)-thioureido]-2-(3-methyl-1,2,4-oxadiazol-5-yl)ethylsulfanylmethyl]-5-methoxy-6-methyl-benzoic acid methyl ester as a colorless oil.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirring
  3. waitwas continued for 1 h at 0° C. and for 10 h at 20° C.
  4. customThe solution was evaporated in vacuo
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-3e96229701eb4478a073c1bc2f597331
Source dataset
uspto-grants-1997_01
Patent number
US05594135

Reaction notes

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