Dichloromethane → HCID 86652011, compound

HRID 1892312Notes

Reaction equation

HRID 1892312 reaction equation
[OH:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C1CCN2C(=NCCC2)CC1.Br[CH2:22][CH2:23][OH:24].C(Cl)[Cl:26]>>[ClH:26].[OH:24][CH2:23][CH2:22][O:1][NH:2][C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 108982-BromoethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 86652011HCID 86652011, compoundYield 70%

Conditions

Temperature
40 °C

Procedure

The title compound was prepared according to the procedure described in WO2006/10094. To a mixture of t-butyl hydroxycarbamate (11.27 g, 85 mmol) and DBU (12.8 mL, 85 mmol) was added 2-bromoethanol (15 mL, 212 mmol) slowly, and the reaction mixture was stirred at 40° C. for 2.5 days. After cooling, the reaction mixture was diluted with DCM, and washed successively with cold 1N HCl aqueous solution, water, and brine. The organic layer was dried over anhydrous Na2SO4, purified by column chromatography (38% EtOAc in hexane) to afford 12.6 g (70%) of the title compound as a colorless syrup. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.95 (s br, 1H), 4.55 (t, 1H), 3.70 (t, 2H), 3.45-3.55 (m, 2H), 1.38 (s, 9H).

Workup

  1. customThe title compound was prepared
  2. temperatureAfter cooling
  3. washwashed successively with cold 1N HCl aqueous solution, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. custompurified by column chromatography (38% EtOAc in hexane)

Sources & evidence

ORD record
ord-9fe984a8cbb34a6395e4cc69e1f6d768
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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