1-Hydroxybenzotriazole → HCID 59331592, compound

HRID 1881812Notes

Reaction equation

HRID 1881812 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].[CH:6]1([CH2:11][CH:12]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:13](O)=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH:6]1([CH2:11][CH:12]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:13]([N:4]([O:3][CH3:2])[CH3:5])=[O:14])[CH2:10][CH2:9][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 120694893-Cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid

Product 1

HCID 59331592HCID 59331592, compoundYield 89.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (80 mL) of N-methoxymethanamine hydrochloride (2.20 g) in N,N-dimethylformamide was added triethylamine (3.10 mL) for neutralization, and 3-cyclopentyl-2-[4-(methylsulfonyl)phenyl]propanoic acid (5.95 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (5.80 g) and 1-hydroxybenzotriazole (4.10 g) were added under ice-cooling. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate, and washed with water, 1N aqueous hydrochloric acid solution and saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (6.07 g, yield 89%) was obtained as colorless amorphous crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 340 (MH+).

Workup

  1. additionwere added under ice-
  2. temperaturecooling
  3. washwashed with water, 1N aqueous hydrochloric acid solution and saturated aqueous sodium hydrogen carbonate
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a05c6be0242343ae883f0b41aea24b33
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…