(2-Bromoethoxy)-tert-butyldimethylsilane → (S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxoazepan-3-ylcarbamate

HRID 912441Notes

Reaction equation

HRID 912441 reaction equation
[O:1]=[C:2]1[C@@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.Br[CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>>[Si:21]([O:20][CH2:19][CH2:18][N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:2]1=[O:1])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 7022178(S)-tert-Butyl (2-oxoazepan-3-yl)carbamate

Product 1

HCID 57736566(S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxoazepan-3-ylcarbamate

Procedure

(S)-tert-butyl 1-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxoazepan-3-ylcarbamate was prepared from compound (S)-tert-butyl 2-oxoazepan-3-ylcarbamate (Example 8) and (2-bromoethoxy)(tert-butyl)dimethylsilane according to the general procedure of Example 9. The crude product was purified by column chromatography, eluting with 25% ethyl acetate/hexanes, to provide compound (2f) in 48% yield.

Workup

  1. customThe crude product was purified by column chromatography
  2. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a45131e9c93346219d985667470407ce
Source dataset
uspto-grants-2011_09
Patent number
US08026233B2

Reaction notes

Loading…