Hexanoyl chloride → Methyl 4-(6-hexanamido-2,3-dihydrobenz-1,4-oxazin-4ylmethyl)-3-methoxybenzoate

HRID 1086544Notes

Reaction equation

HRID 1086544 reaction equation
[C:1](Cl)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=3[O:30][CH3:31])[C:14]=2[CH:32]=1>ClCCl>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=3[O:30][CH3:31])[C:14]=2[CH:32]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 67340Hexanoyl chlorideHCID 14763126Methyl 4-(6-amino-2,3-dihydrobenz-1,4-oxazin4-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365905Methyl 4-(6-hexanamido-2,3-dihydrobenz-1,4-oxazin-4ylmethyl)-3-methoxybenzoateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Hexanoyl chloride (0.084 g.) was added to a stirred solution of methyl 4-(6-amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)-3-methoxybenzoate (L) (0.2 g.) in dichloromethane (20 ml.), under an atmosphere of nitrogen. The mixture was stirred for one hour and then diluted with dichloromethane (40 ml.). This mixture was washed with water, dried (MgSO4) and evaporated. The residual oil was dissolved in 3:7 v/v ethyl acetate:hexane, and the solution obtained was allowed to filter through a short column of silica gel, washing with one column volume of the same solvent mixture. Evaporation of the column eluate gave the title compound (0.212 g., 82%), as a foam: NMR (250 MHz, CDCl3) 0.9(t,3H, CH2CH3), 1.3(m,4H, CH3.CH2.CH2), 1.6(m,2H, CH2.CH2.CON), 2.2(t,2H, CH2.CON), 3.35(t,2H, OCH2.CH2N), 3.9(br s,6H, OCH3 + CO.OCH3), 4.2(t,2H, OCH2.CH2N), 4.5(s,2H, CH2 --Ar), 6.8(m,3H), 6.9(br s,1H, NH), 7.2(m,1H), 7.5(m, 2H).

Workup

  1. washThis mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. dissolutionThe residual oil was dissolved in 3:7 v/v ethyl acetate
  5. customhexane, and the solution obtained
  6. filtrationto filter through a short column of silica gel
  7. washwashing with one column volume of the same solvent mixture
  8. customEvaporation of the column eluate

Sources & evidence

ORD record
ord-555f11430437453bb3da3dab71059f95
Source dataset
uspto-grants-1991_07
Patent number
US05030643

Reaction notes

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