Triethylamine → HCID 88472595, compound

HRID 365043Notes

Reaction equation

HRID 365043 reaction equation
[CH2:1]([C:11]1[CH:21]=[CH:20][C:14]([C:15]([N:17]([OH:19])[CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:22](=[O:24])=[O:23].[CH3:25][C:26]([CH3:28])=O.[CH2:29](OC(Cl)=O)[CH:30]([CH3:32])[CH3:31].[CH3:37][CH2:38]N(CC)CC>CC(C)=O>[CH:1](/[C:11]1[CH:12]=[CH:13][C:14]([C:15]([N:17]([O:19][CH2:31][C:30]2[CH:32]=[CH:28][CH:26]=[CH:25][CH:29]=2)[CH2:18][CH2:37][CH2:38][C:22]([OH:24])=[O:23])=[O:16])=[CH:20][CH:21]=1)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 136728004-Decyl-N-hydroxy-N-methylbenzamideHCID 18522661Acetone cardice2×

Product 1

HCID 88472595HCID 88472595, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-10 °C

Procedure

To a magnetically stirred solution of the benzoic acid (prepared as in Example 1 Part C) (1.97 g, 7.57 mM) in dry acetone (20 ml) at -10° C. (dry ice/acetone) and under argon was added isobutylchloroformate (1.1 ml, 8.48 mM) followed by Et3N (1.2 ml, 7.57 mM). This was stirred for 30 minutes at -10° C., then filtered into a cooled solution (-15° C.) of the hydrolysis product prepared as described in Example 4 Part D(1). The resulting mixture was stirred for 30 minutes at -10° C. (dry ice/acetone) then allowed to warm to room temperature and stirred overnight. The reaction mixture was then partitioned between EtOAc and 5% KHSO4. The organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to a yellow oil (5.0 g). A flash chromatography on LPS-1 silica gel eluting with (7:1) CH2Cl2 -acetone yielded 680 mg (20%) of the title amide as a white solid with consistent NMR spectral data.

Workup

  1. filtrationfiltered into a cooled solution (-15° C.) of the hydrolysis product
  2. customprepared
  3. temperatureto warm to room temperature
  4. stirringstirred overnight
  5. customThe reaction mixture was then partitioned between EtOAc and 5% KHSO4
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo to a yellow oil (5.0 g)

Sources & evidence

ORD record
ord-d370b508bcf243df84b8a5f35b876c2f
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

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