Diisopropylethylamine → HCID 70946581, compound

HRID 1866555Notes

Reaction equation

HRID 1866555 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:16]Br)=[CH:11][C:10]=1[CH2:26][OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:28][C:29]([CH3:42])([CH3:41])[CH2:30][C:31]1[CH:32]=[C:33]([CH2:37][C:38]([OH:40])=[O:39])[CH:34]=[CH:35][CH:36]=1.[CH:43](N(CC)C(C)C)(C)C>CS(C)=O.C(OCC)(=O)C>[CH3:43][O:39][C:38](=[O:40])[CH2:37][C:33]1[CH:34]=[CH:35][CH:36]=[C:31]([CH2:30][C:29]([NH:28][CH2:16][C@@H:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]([CH2:26][OH:27])[CH:11]=2)[O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])([CH3:42])[CH3:41])[CH:32]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanolHCID 68717856HCID 68717856, compound

Product 1

HCID 70946581HCID 70946581, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl) phenyl]methanol (preparation 23), (3.4 g, 7.5 mmol), [3-(2-amino-2-methylpropyl)phenyl]acetic acid (preparation 146), (1.7 g, 7.5 mmol) and N,N-diisopropylethylamine (1.4 mL, 8 mmol) in dimethylsulfoxide (7.5 mL) was stirred at 90° C. for 28 hours. The reaction mixture was then cooled, diluted with ethyl acetate and washed with water. The organic solution was then dried over magnesium sulfate, concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate:pentane, 66:33, to afford the title compound as a colourless oil in 50% yield, 2.2 g. 1H NMR (400 MHz, CDCl3) δ: 7.44-7.31 (6H, m), 7.30-7.19 (3H, m), 7.13-7.05 (2H, m), 6.80 (1H, d), 4.75-4.66 (3H, m), 3.68 (3H, s), 3.59 (2H, s), 2.90-2.72 (4H, m), 1.22-1.09 (6H, m), 0.70 (9H, s), −0.06 (3H, s), −0.28 (3H, s) ppm.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with water
  3. dry with materialThe organic solution was then dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-010eecc605bd428e92b92bee9320d7f1
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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