Hydrochloric Acid → HCID 86597662, compound

HRID 350754Notes

Reaction equation

HRID 350754 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([CH:6]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[OH:7])=[CH:4][CH:3]=1.[N:18]1([C:27]2[O:28][C:29]([CH2:39][CH2:40][C:41](O)=[O:42])=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[N:31]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[N:18]1([C:27]2[O:28][C:29]([CH2:39][CH2:40][C:41]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH:6]([P:8]([O:9][CH2:10][CH3:11])([O:12][CH2:13][CH3:14])=[O:15])[OH:7])=[CH:16][CH:17]=3)=[O:42])=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)[N:31]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[CH:19]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 21088585HCID 21088585, compoundHCID 23061737Diethyl P-[(4-aminophenyl)hydroxymethyl]phosphonate

Product 1

HCID 86597662HCID 86597662, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of diethyl 4-amino-α-hydroxybenzylphosphonate (50 mg), 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (54 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (38 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (43 mg) and N,N-dimethylformamide (0.5 ml) was stirred overnight at room temperature. To the reaction mixture was added 0.1N aqueous hydrochloric acid solution (2 ml) and the reaction mixture was extracted with ethyl acetate (2 ml). The organic layer was concentrated, introduced into preparative HPLC and purified to give 3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]-N-(4-[(diethylphosphono)(hydroxy)methyl]phenyl}propionamide (52 mg, 58%). Recrystallization from ethyl acetate-isopropyl ether gave yellow prism crystals. melting point: 171–172° C. MS (ESI+): 609 (M+H)

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (2 ml)
  2. concentrationThe organic layer was concentrated
  3. additionintroduced into preparative HPLC
  4. custompurified

Sources & evidence

ORD record
ord-7b4ec0dce8374ff9a23c02e94f45fe50
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

Loading…