Hydrochloric Acid → HCID 57476890, compound

HRID 2368397Notes

Reaction equation

HRID 2368397 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([OH:9])=O)[CH3:2].[NH2:16][C:17]([CH3:23])([CH3:22])[C:18]([O:20]C)=[O:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Li+].[OH-].Cl>CN(C=O)C.O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([NH:16][C:17]([CH3:23])([CH3:22])[C:18]([OH:20])=[O:19])=[O:9])[CH3:2]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 794173,4-Diethoxybenzoic acidHCID 81531DiisopropylethylamineHCID 4186341Methyl 2-amino-2-methylpropanoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57476890HCID 57476890, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

210 mg of 3,4-diethoxybenzoic acid and 160 mg of methyl aminoisobutyrate were stirred in 3 ml of DMF at room temperature. It was treated with 440 mg of HATU and 0.4 ml of DIEA at the same temperature and the reaction was stirred for 2 days. The reaction was monitored by LC-MS, which indicated complete consumption of the starting materials. Product LC-MS (m/z 310.1). This crude reaction mixture was then diluted with 3 ml of water followed by an addition of 250 mg of LiOH. The reaction mixture was stirred at room temperature overnight and the LC-MS analysis indicated the reaction was completed. The reaction mixture was neutralized by 6N-HCl and the resulting creamy precipitates were collected by filtration and washed with water (50 ml). Drying the filter cake yielded the title compound. m/z 296.1 (MH+).

Workup

  1. customconsumption of the starting materials
  2. customThis crude reaction mixture
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. customthe resulting creamy precipitates
  5. filtrationwere collected by filtration
  6. washwashed with water (50 ml)
  7. customDrying the filter cake

Sources & evidence

ORD record
ord-d09e2ce431784f3f862ff511a0933a5b
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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