Acetic Anhydride → HCID 68185408, compound

HRID 2366898Notes

Reaction equation

HRID 2366898 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][CH2:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:12]=2)[C@H:7]([NH:19][C:20](=[O:25])[O:21][CH:22]([CH3:24])[CH3:23])[CH2:6][C@@H:5]1[CH3:26])(=[O:3])[CH3:2].[C:27](OC(=O)C)(=[O:29])[CH3:28]>>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]([C:27](=[O:29])[CH3:28])[CH2:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:12]=2)[C@H:7]([NH:19][C:20](=[O:25])[O:21][CH:22]([CH3:23])[CH3:24])[CH2:6][C@@H:5]1[CH3:26])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 68185410HCID 68185410, compound

Product 1

HCID 68185408HCID 68185408, compoundYield 49%

Procedure

1-Methylethyl {(2S,4R)-1-acetyl-2-methyl-6-[(2-oxopropyl)amino]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation see Intermediate 111) (200 mg, 0.553 mmol) was dissolved in acetic anhydride (1044 μl, 11.07 mmol) and the resulting mixture was stirred at room temperature under nitrogen for 1 h then partitioned between water (2 mL) and DCM (5 mL). The layers were separated and the organic phase washed with water, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 10 to 100% AcOEt in hexanes) gave 1-methylethyl {(2S,4R)-1-acetyl-6-[acetyl(2-oxopropyl)amino]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (130 mg, 0.274 mmol, 49%) as an orange oil.

Workup

  1. customthen partitioned between water (2 mL) and DCM (5 mL)
  2. customThe layers were separated
  3. washthe organic phase washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (gradient: 10 to 100% AcOEt in hexanes)

Sources & evidence

ORD record
ord-5fe9ce1603c9412baa7fd831d20b072b
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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