Acetic Anhydride → HCID 86669276, compound

HRID 2366957Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:11][C@@H: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][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:23]=3)[CH:8]=2)[NH:3]1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>>[C:32]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:19]3[N:20]=[CH:21][N:22]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[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:34])[CH3:33]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 86669238HCID 86669238, compound

Product 1

HCID 86669276HCID 86669276, compoundYield 78%

Procedure

A solution of 1,1-dimethylethyl {(cis)-4-[2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazol-1-yl}acetate (for a preparation see Intermediate 88) (1.0 g, 2.33 mmol) in acetic anhydride (2 mL) was allowed to stand at room temperature for 16 h then most of the solvent was concentrated in vacuo. The residue was co-evaporated twice with toluene. Purification of the resulting residue by flash chromatography on silica gel (gradient: 0 to 2% MeOH in DCM) gave 1,1-dimethylethyl {(cis)-4-[1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]-1H-imidazol-1-yl}acetate (862 mg, 1.832 mmol, 78%) as a pale yellow solid.

Workup

concentrationmost of the solvent was concentrated in vacuo
customPurification of the resulting residue by flash chromatography on silica gel (gradient: 0 to 2% MeOH in DCM)

Sources & evidence

ORD record: ord-fa0de8b050064af99a98663a3abf34b3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697725B2

Reaction notes

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