Hydrochloric Acid → N-methylsulfonyl-1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxamide

HRID 278501Notes

Reaction equation

HRID 278501 reaction equation
[CH2:1]([O:8][C@H:9]([C@H:11]([N:24]1[CH:28]=[C:27]([C:29](O)=[O:30])[N:26]=[CH:25]1)[CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][S:33]([NH2:36])(=[O:35])=[O:34].Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C1C=CN=CC=1.CN(C)C=O.O.C(OCC)(=O)C>[CH3:32][S:33]([NH:36][C:29]([C:27]1[N:26]=[CH:25][N:24]([C@H:11]([CH2:12][CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)[C@@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:10])[CH:28]=1)=[O:30])(=[O:35])=[O:34]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573122811-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxylic acid

Product 1

HCID 57234468N-methylsulfonyl-1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxamideYield 27.6%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxylic acid (obtained in Example 30)(55 mg), methanesulfonamide (12.7 mg), 4-dimethylaminopyridine (24.3 mg), and 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (51.2 mg) in N,N-dimethylformamide (2 ml) was stirred at room temperature for three days. Ethyl acetate and water were added, and the whole was acidified to pH 3 with hydrochloric acid. The organic layer was dried and evaporated. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (20:1) to give a pale yellow gummy oil of N-methylsulfonyl-1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxamide (18 mg).

Workup

  1. customThe organic layer was dried
  2. customevaporated
  3. customThe residue was purified by column chromatography on silica gel
  4. washeluting with a mixture of dichloromethane and methanol (20:1)

Sources & evidence

ORD record
ord-7f00db0211e449cb896c92fafcfcd902
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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