Chloroform → HCID 59409903, compound

HRID 2066813Notes

Reaction equation

HRID 2066813 reaction equation
[CH2:1]([NH:8][CH2:9][C@H:10]([OH:13])[CH2:11][Cl:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.C(NC(C)C)(C)C.[C:25](N1C=CN=C1)(N1C=CN=C1)=[O:26]>ClCCl.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:9][C@@H:10]([CH2:11][Cl:12])[O:13][C:25]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 7912DiisopropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 6931954HCID 6931954, compound2×

Product 1

HCID 59409903HCID 59409903, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a 250 ml round bottom flask was added (2S)-1-(benzylamino)-3-chloropropan-2-ol (1.0 g, 5 mmol, INTERMEDIATE 12), chloroform (15 ml), and diisopropylamine (3.23 g, 25 mmol). To this was added carbonyldiimidazole (1.63 g, 10 mmol), and the mixture was heated to 45° C. for 15 h. The reaction then was diluted with dichloromethane (25 ml) and washed with water. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to provide a pale tan residue. The product was isolated on silica gel eluting with a gradient of ethyl acetate in hexanes from 0% to 100% to provide 750 mg of product as colorless oil. Mass spectrum (ESI) 226.1 (M+1).

Workup

  1. customThe reaction
  2. washwashed with water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a pale tan residue

Sources & evidence

ORD record
ord-0105e70e820041a2ab4512bdfe36b58b
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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