1-Hydroxybenzotriazole → HCID 59331445, compound

HRID 1881844Notes

Reaction equation

HRID 1881844 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].[CH:6]1([S:9]([C:12]2[CH:17]=[CH:16][C:15](/[C:18](=[CH:22]\[CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)/[C:19](O)=[O:20])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:8][CH2:7]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH:6]1([S:9]([C:12]2[CH:13]=[CH:14][C:15](/[C:18](=[CH:22]\[CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)/[C:19]([N:4]([O:3][CH3:2])[CH3:5])=[O:20])=[CH:16][CH:17]=2)(=[O:10])=[O:11])[CH2:8][CH2:7]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 56971691(2E)-2-[4-(Cyclopropanesulfonyl)phenyl]-3-(oxan-4-yl)prop-2-enoic acid

Product 1

HCID 59331445HCID 59331445, compoundYield 101.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methoxymethanamine hydrochloride (350 mg) in N,N-dimethylformamide (10 mL) was added triethylamine (500 μL), and the mixture was stirred at room temperature for 30 min. (2E)-2-[4-(Cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)propan-2-enoic acid (1.00 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (860 mg) and 1-hydroxybenzotriazole (600 mg) were added to the reaction mixture under ice-cooling, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate, washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated to give a crude product (1.15 g) of the title compound as colorless crystals. MS: 380 (MH+).

Workup

  1. additionwere added to the reaction mixture under ice-
  2. temperaturecooling
  3. washwashed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eed18930cd724a909275d17606da7002
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…