Sodium Hydroxide → HCID 86601012, compound

HRID 1875709Notes

Reaction equation

HRID 1875709 reaction equation
[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:9][C@H:10]([OH:13])[CH2:11]Cl)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:14])[N:7]([CH3:8])[CH2:9][C@H:10]1[CH2:11][O:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86601011HCID 86601011, compound

Product 1

HCID 86601012HCID 86601012, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

((S)-3-chloro-2-hydroxypropyl)-methylcarbamic acid tert-butyl ester (2.23 g, 10 mmol) was dissolved in THF (30 mL), and then an aqueous sodium hydroxide solution (0.48 g in 10 mL water) was added. The mixture was stirred for 2 h. The mixture was then concentrated under reduced pressure to remove most of the THF, and the remaining aqueous solution was extracted into ethyl acetate, washing with water. The product was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title intermediate as an oil (1.6 g). (m/z): [M+Na]+ calcd for C9H17NO3, 210.10; found 210.1. 1H-NMR (DMSO d6, 299.96 MHz): δ (ppm) 1.32-1.42 (s, 9H), 2.69-2.73 (m, 1H), 2.75-2.85 (s, 3H), 2.95-3.05 (br s, 1H), 3.10-3.15 (dm, 1H), 3.16-3.21 (d, 1H), 3.37-3.51 (m, 2H).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customto remove most of the THF
  3. extractionthe remaining aqueous solution was extracted into ethyl acetate
  4. washwashing with water
  5. dry with materialThe product was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-383bfdad9d8e4e188181c4297375543e
Source dataset
uspto-grants-2012_11
Patent number
US08309575B2

Reaction notes

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