Diethyl Ether → HCID 58124867, compound

HRID 1971663Notes

Reaction equation

HRID 1971663 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:15](=O)[C:16]([N:18]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]#[C:25][C:26]3[S:30][CH:29]=[N:28][CH:27]=3)=[O:17])[CH:9]2C(O)=O)=[CH:4][C:3]=1[O:36][CH3:37].C([O-])(=O)C.[Na+].[NH4+].[OH-].C(OCC)C>C(OC(=O)C)(=O)C.O>[Br:1][C:2]1[C:3]([O:36][CH3:37])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:15]4[C:16](=[O:17])[N:18]([C:31]([CH3:34])([CH3:32])[CH3:33])[CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]=4[C:25]([C:26]4[S:30][CH:29]=[N:28][CH:27]=4)=[C:9]3[C:10]=2[CH:11]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 581247927-Bromo-2-(2-(tert-butyl(3-(3-(thiazol-5-yl)prop-2-ynyloxy)propyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Product 1

HCID 58124867HCID 58124867, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 240 mg of 8d and 250 mg of sodium acetate in 5 ml of acetic anhydride was heated at 100° C. for 30 min. The reaction mixture was cooled, diluted with 10 ml of water and stirred for 1 hr at ambient temperature to hydrolyze excess anhydride. The mixture was then made alkaline with cold conc. aq. NH4OH and the product was extracted with ethyl acetate. The product thus isolated was purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate as eluent. The purified product isolated was treated with diethyl ether and gave 150 mg of crystalline material 8e. Rf (toluene/acetone 7/3) 0.50.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe product was extracted with ethyl acetate
  3. customThe product thus isolated
  4. customwas purified by chromatography over silica gel
  5. customThe purified product isolated

Sources & evidence

ORD record
ord-5012570b1c5c42938c145af98be34598
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…