Acetic Anhydride → HCID 52934563, compound

HRID 2366951Notes

Reaction equation

HRID 2366951 reaction equation
[CH3:1][CH:2]1[CH2:11][CH:10]([NH:12][C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:19]3[N:20]=[CH:21][N:22]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]=3)[CH:8]=2)[NH:3]1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>>[C:33]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:19]3[N:20]=[CH:21][N:22]([CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:23]=3)=[CH:6][CH:5]=2)[C@H:10]([NH:12][C:13]([O:15][CH:16]([CH3:17])[CH3:18])=[O:14])[CH2:11][C@@H:2]1[CH3:1])(=[O:35])[CH3:34]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 68162171HCID 68162171, compound

Product 1

HCID 52934563HCID 52934563, compoundYield 66%

Procedure

A solution of 1,1-dimethylethyl 3-{-4-[2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazol-1-yl}propanoate (for a preparation see Intermediate 93) (1.46 g, 3.3 mmol) in acetic anhydride (3 mL) was allowed to stand at room temperature for 16 h then most of the solvent was removed in vacuo. The residue was co-evaporated twice with toluene. Its purification by flash chromatography on silica gel (gradient: 0 to 2% MeOH in DCM) gave 1,1-dimethylethyl 3-{(cis)-4-[1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazol-1-yl}propanoate (1.055 g, 2.177 mmol, 66%) as a colourless solid.

Workup

  1. custommost of the solvent was removed in vacuo
  2. customIts purification by flash chromatography on silica gel (gradient: 0 to 2% MeOH in DCM)

Sources & evidence

ORD record
ord-22b40d93ac004f95ae6c2cd151577ead
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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