Benzyl chloroformate → HCID 86607615, compound

HRID 2357614Notes

Reaction equation

HRID 2357614 reaction equation
[OH:1][C@H:2]([CH3:9])[CH2:3][NH:4][C@H:5]([CH3:8])[CH2:6][OH:7].C(=O)(O)[O-].[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>ClCCl>[OH:7][CH2:6][C@H:5]([N:4]([CH2:3][C@H:2]([OH:1])[CH3:9])[C:16](=[O:17])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:8]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 55298733HCID 55298733, compound

Product 1

HCID 86607615HCID 86607615, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (R)-2-((R)-2-hydroxypropylamino)propan-1-ol (11 g, 83 mmol) in 200 mL dichloromethane stirred at 0° C. was added a sat. solution of sodium bicarbonate (8.3 g, 99 mmol), then added dropwise benzyl chloroformate (15 g, 91 mmol). The mixture was stirred from 0° C. warming to RT over 4 h. The mixture was extracted with dichloromethane (3×100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by column eluting with 20-70% ethyl acetate in hexane to give the benzyl (R)-1-hydroxypropan-2-yl((R)-2-hydroxypropyl)carbamate as a colorless oil.

Workup

  1. stirringThe mixture was stirred from 0° C.
  2. temperaturewarming to RT over 4 h
  3. extractionThe mixture was extracted with dichloromethane (3×100 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column
  8. washeluting with 20-70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b88279d80e504e22bf0ce907e04bd878
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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