Water → HCID 131725390, compound

HRID 1744784Notes

Reaction equation

HRID 1744784 reaction equation
[CH3:1][CH:2]1[C:7]([CH:9]=[O:10])([CH3:8])[CH2:6][CH2:5][CH:4]=[CH:3]1.[CH3:11][O:12][C:13](=[O:21])[CH:14]([CH2:19][OH:20])[NH:15][CH:16]([CH3:18])[CH3:17].ClC1C=CC=C(Cl)C=1C(O)=O.O>C1(C)C=CC=CC=1>[CH3:1][CH:2]1[C:7]([CH:9]=[O:10])([CH3:8])[CH2:6][CH2:5][CH:4]=[CH:3]1.[O:12]1[CH2:13][CH2:14][NH:15][CH2:16]1.[CH3:11][O:12][C:13](=[O:21])[CH:14]([CH2:19][OH:20])[NH:15][CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 57582,6-Dichlorobenzoic acidHCID 3034463TRIPLALHCID 22223452HCID 22223452, compound

Product 1

HCID 131725390HCID 131725390, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of triplal (2, 1.0 equiv), N-isopropyl-DL-serine methyl ester (1, 1.05 equiv) and 2,6-dichlorobenzoic acid (0.01 equiv) is refluxed 6 hours in toluene during which time water is removed by azeotropic distillation. The solution is cooled, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and filtered. The toluene is subsequently removed under reduced pressure to yield the desired product, 3.

Workup

  1. customis removed by azeotropic distillation
  2. temperatureThe solution is cooled
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe toluene is subsequently removed under reduced pressure

Sources & evidence

ORD record
ord-5a6081f3dd434799bd4da9aa5ff22b94
Source dataset
uspto-grants-2006_03
Patent number
US07018978B2

Reaction notes

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