2-Bromoethyl methyl ether → HCID 69472218, compound

HRID 1180428Notes

Reaction equation

HRID 1180428 reaction equation
[CH3:1][CH:2]([CH3:29])[CH2:3][C@H:4]([O:9][C@H:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:30][O:31][CH2:32][CH2:33][Br:34]>C(#N)C>[Br-:34].[CH3:8][O:7][C:5]([C@@H:4]([O:9][C@H:10]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[N+:19]([CH2:33][CH2:32][O:31][CH3:30])[CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:12]=1)[CH2:3][CH:2]([CH3:29])[CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 86605395HCID 86605395, compound

Product 1

HCID 69472218HCID 69472218, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl (2S)-4-methyl-2-{[(R)-phenyl(4-pyridin-3-ylphenyl)methyl]oxy}pentanoate from example 36 step 2 (740 mg, 1.9 mmol) and 2-bromoethyl methyl ether (1.32 g, 9.5 mmol) in acetonitrile (10 mL) was heated in a pressure tube emersed in an oil bath at 120+ C. for 18 hours. The mixture was concentrated and the residue slurried with diethyl ether (25 mL) 2 times followed by decanting and then pumped on by high vacuum to obtain the title compound as a foam.

Workup

  1. customemersed in an oil bath at 120+ C
  2. concentrationThe mixture was concentrated
  3. customby decanting

Sources & evidence

ORD record
ord-d9354dcf94ac4f7bb2c9fe67aa7b54c1
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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