Acetic Acid → HCID 58070090, compound

HRID 1472299Notes

Reaction equation

HRID 1472299 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:6].C([O-])([O-])=O.[K+].[K+].C(O)(=O)C.[CH3:39][NH:40][CH3:41]>C1COCC1.O>[CH3:39][N:40]([CH3:41])[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 11430Potassium CarbonateHCID 58070056HCID 58070056, compound

Product 1

HCID 58070090HCID 58070090, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The Bromoacid 13 (2 mmol) is dissolved in 2M solution of dimethylamine in THF (20 mL) and to it 1 g of anhydrous K2CO3 was added and the mixture was heated in a pressure bottle at 50° C. overnight. The TLC showed the completion of the reaction. The reaction mixture was acidified with acetic acid and diluted with water (100 mL) and extracted with dichloromethane (2×60 mL). The combined organic layers were concentrated dried and used as such in the next reaction. MW calcd for C23H43NO6 429.59. Found 430.6 (MH)+.

Workup

  1. additionwas added
  2. customthe completion of the reaction
  3. extractionextracted with dichloromethane (2×60 mL)
  4. concentrationThe combined organic layers were concentrated
  5. customdried
  6. customsuch in the next reaction

Sources & evidence

ORD record
ord-d804079741e740d1aa479b4e68c5ae43
Source dataset
uspto-grants-2015_04
Patent number
US09012498B2

Reaction notes

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