tert-Butyldimethylsilyl chloride → (4S,5S)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-(4-(2-methoxyethoxy)phenyl)-oxazolidin-2-one

HRID 929949Notes

Reaction equation

HRID 929949 reaction equation
[OH:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:10][CH:9]=2)[O:6][C:5](=[O:19])[NH:4]1.[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22]>>[Si:24]([O:1][CH2:2][C@H:3]1[C@H:7]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:12][CH:13]=2)[O:6][C:5](=[O:19])[NH:4]1)([C:21]([CH3:23])([CH3:22])[CH3:20])([CH3:26])[CH3:25]

Participants

3

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 86718530(4S,5S)-4-(Hydroxymethyl)-5-(4-(2-methoxyethoxy)phenyl)oxazolidin-2-one

Product 1

HCID 86718531(4S,5S)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-5-(4-(2-methoxyethoxy)phenyl)-oxazolidin-2-one

Procedure

The title compound was prepared in analogy to the procedure described for intermediate 10 [(4S,5S)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-5-(4-methoxyphenyl)oxazolidin-2-one] from (4S,5S)-4-(hydroxymethyl)-5-(4-(2-methoxyethoxy)phenyl)oxazolidin-2-one and TBDMS-Cl to afford after purification by column chromatography (using EtOAc in heptane from 5% to 50%) intermediate 11 as a light yellow oil. TLC (heptane/EtOAc 1:1) Rf=0.26; tR=1.28 min (UPLC 1); LC-MS: [M+H] 382.2; Rt 1.17 min; (LCMS method 2); 1H NMR (400 MHz, CDCl3): 7.30 (d, 2H), 6.97 (d, 2H), 5.44 (br s, 1H), 5.23 (d, 1H), 4.18 (dd, 2H), 3.70-3.85 (m, 5H), 3.48 (s, 3H), 0.91 (s, 9H), 0.11 (s,

Workup

  1. customto afford
  2. customafter purification by column chromatography (using EtOAc in heptane from 5% to 50%) intermediate 11 as a light yellow oil

Sources & evidence

ORD record
ord-8dbb174f0d124b9699e86a15c0c9200b
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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