Dimethylamine, hydrochloride → HCID 59909781, compound

HRID 2183074Notes

Reaction equation

HRID 2183074 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][C@H:8]([C:12]1[O:13][CH:14]=[C:15]([C:17](O)=[O:18])[N:16]=1)[CH2:9][CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:33][NH:34][CH3:35].C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH3:33][N:34]([CH3:35])[C:17]([C:15]1[N:16]=[C:12]([C@H:8]([CH2:9][CH:10]=[CH2:11])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:20])[O:13][CH:14]=1)=[O:18]

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59909741HCID 59909741, compound

Product 1

HCID 59909781HCID 59909781, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-3-butenyl]-1,3-oxazole-4-carboxylic acid (Preparation 116) (10.77 g, 38.3 mmol) in dichloromethane (250 ml), at 0° C., was treated with 1-hydroxybenzotriazole hydrate (5.75 g, 42.6 mmol), dimethylamine hydrochloride (3.45 g, 42.3 mmol) and N,N-diisopropylethylamine (13 ml, 75.13 mmol) and lastly 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.10 g, 42.3 mmol), allowed to warm to room temperature and stirred for 20 hours under a nitrogen atmosphere. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, aqueous citric acid (10%), water and brine, dried over anhydrous sodium sulphate and filtered. The solvent was removed under reduced pressure. The oil was purified by column chromatography on silica gel eluting with a solvent gradient of 7:3 (pentane:ethyl acetate) gradually changing to 1:1 (pentane:ethyl acetate) to afford the title compound as a colourless oil (9.9 g).

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution, aqueous citric acid (10%), water and brine
  2. dry with materialdried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure
  5. customThe oil was purified by column chromatography on silica gel eluting with a solvent gradient of 7:3 (pentane:ethyl acetate)

Sources & evidence

ORD record
ord-b1ad80d91f694dba8f64cf74d3067414
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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