Water → HCID 68455295, compound

HRID 2357639Notes

Reaction equation

HRID 2357639 reaction equation
[CH2:1]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].O>ClCCl>[CH2:1]([N:8]([C@H:9]([CH3:12])[CH2:10][OH:11])[C:15](=[O:16])[CH2:14][Cl:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 7353896(2R)-2-(Benzylamino)propan-1-ol

Product 1

HCID 68455295HCID 68455295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

(R)-2-(Benzylamino)propan-1-ol (16.58 g, 100 mmol) was dissolved in dichloromethane (125 mL) and TEA (18.1 mL, 130 mmol) before being cooled to −10° C. in a methanol/ice bath. Chloroacetic acid chloride (8.78 mL, 110 mmol) was added dropwise and the mixture was stirred for 1.5 h at −10° C. A small amount of water was then added to remove the amine. The reaction mixture was poured into a separatory funnel, washed 2×50 mL with dichloromethane, separated, organic layers dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography to give the title compound.

Workup

  1. customto remove the amine
  2. additionThe reaction mixture was poured into a separatory funnel
  3. washwashed 2×50 mL with dichloromethane
  4. customseparated
  5. dry with materialorganic layers dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b46a847f917d45a9a678cb63082929e2
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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