Dimethylamine → HCID 21967812, compound

HRID 1003275Notes

Reaction equation

HRID 1003275 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][NH:27][CH3:28]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][C:23]([N:27]([CH3:28])[CH3:26])=[O:25])=[CH:14][CH:15]=2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 54067144HCID 54067144, compound

Product 1

HCID 21967812HCID 21967812, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(S)-4-[2-(tert-Butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yloxy]butyric acid (399 mg) was dissolved in tetrahydrofuran (5 ml), and N,N'-carbonyldiimidazole (204 mg) was added to the solution under ice-cooling with stirring. After reaction for 2 hours, a solution of dimethylamine (1.40 g) in tetrahydrofuran (2 ml) was added to the reaction mixture under ice-cooling with stirring. After reaction for 45 minutes and then at room temperature for 45 minutes, the reaction mixture was concentrated in vacuo. Water was added to the resulting residue and the mixture was extracted with diethyl ether. The extract was washed with 10% aqueous citric acid solution, water, a saturated aqueous sodium bicarbonate solution and water successively, and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give (S)-4-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylbutyramide (396 mg) having a melting point of 97-101° C.

Workup

  1. temperaturecooling
  2. customAfter reaction for 2 hours
  3. temperaturecooling
  4. stirringwith stirring
  5. customAfter reaction for 45 minutes
  6. concentrationthe reaction mixture was concentrated in vacuo
  7. additionWater was added to the resulting residue
  8. extractionthe mixture was extracted with diethyl ether
  9. washThe extract was washed with 10% aqueous citric acid solution, water
  10. dry with materiala saturated aqueous sodium bicarbonate solution and water successively, and dried over anhydrous magnesium sulfate
  11. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ab793385dd14414ebab95d0c36972c11
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

Loading…