Diisopropylethylamine → HCID 69067295, compound

HRID 643170Notes

Reaction equation

HRID 643170 reaction equation
C(N(C(C)C)C(C)C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH2:18][C@@H:19]([OH:24])[C:20]([O:22][CH3:23])=[O:21])[CH:14]=[CH:15][C:16]=1[OH:17].Cl[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31]>C(Cl)Cl>[Br:10][C:11]1[CH:12]=[C:13]([CH2:18][C@@H:19]([OH:24])[C:20]([O:22][CH3:23])=[O:21])[CH:14]=[CH:15][C:16]=1[O:17][CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether2×HCID 69071944HCID 69071944, compound

Product 1

HCID 69067295HCID 69067295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6.7 mL (39.1 mmol) ethyldiisopropylamine were added to a solution of 10.2 g (34.6 mmol) methyl (R)-3-(3-bromo-4-hydroxy-phenyl)-2-hydroxy-propionate in 100 mL DCM and the reaction mixture was cooled in the ice bath. Then a solution of 7.9 mL (44.6 mmol) (2-chloromethoxy-ethyl)-trimethyl-silane in 20 mL DCM was added. The reaction mixture was stirred for 3 h at RT and then combined with another 0.67 mL ethyldiisopropylamine and 0.8 mL (4.5 mmol) (2-chloromethoxy-ethyl)-trimethyl-silane to complete the reaction and stirred for 1.5 h at RT. The reaction mixture was washed with 5% Na2CO3 solution and saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent had been eliminated the residue was purified by chromatography (silica gel, Cyc/EtOAc 75:25).

Workup

  1. customthe reaction
  2. stirringstirred for 1.5 h at RT
  3. washThe reaction mixture was washed with 5% Na2CO3 solution and saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customwas purified by chromatography (silica gel, Cyc/EtOAc 75:25)

Sources & evidence

ORD record
ord-f6dd6acda94242ae9c4b9c94581fb339
Source dataset
uspto-grants-2010_04
Patent number
US07696209B2

Reaction notes

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