Ethanolamine → HCID 21894500, compound

HRID 720691Notes

Reaction equation

HRID 720691 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].CN1CCOCC1.C(O[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])C.[C:21]1([C:27](Cl)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[F:19][C:16]([F:17])([F:18])[C:15]([NH:4][CH2:3][CH2:1][O:2][C:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:20]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 6456Trityl chlorideHCID 79724-MethylmorpholineHCID 9794Ethyl trifluoroacetate

Product 1

HCID 21894500HCID 21894500, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 200 mL of dichloromethane was added 100 mmole of ethanolamine, 200 mmole of N-methylmorpholine and 105 mmole of ethyltrifluoroacetate. This solution was allowed to stir for 30 minutes and then 105 mmol of triphenylmethyl chloride was added. After stirring overnight, the solution was transferred to a separatory fimnel and washed twice with water. The organic layer was dried with sodium sulfate, filtered and evaporated to a yellow oil. The product was determined to be impure and was redissolved in DCM and washed with 5% monobasic sodium phosphate and then a mixture of 10% citric acid and 5% monobasic sodium phosphate. The organic layer was dried with sodium sulfate, filtered and evaporated to a yellow oil. The residue was crystallized from methanol but this caused the impurity to crystallized. The mother liquor was then recrystallized from hexanes/ethyl acetate to yield 9.0 g of crystaline N-(trifluoroacetyl)-O-(trityl)-ethanolamine.

Workup

  1. stirringAfter stirring overnight
  2. washwashed twice with water
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated to a yellow oil
  6. dissolutionwas redissolved in DCM
  7. washwashed with 5% monobasic sodium phosphate
  8. additiona mixture of 10% citric acid and 5% monobasic sodium phosphate
  9. dry with materialThe organic layer was dried with sodium sulfate
  10. filtrationfiltered
  11. customevaporated to a yellow oil
  12. customThe residue was crystallized from methanol
  13. customto crystallized
  14. customThe mother liquor was then recrystallized from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e0d761725a954e3fbb7ceb645c0fbb32
Source dataset
uspto-grants-2006_11
Patent number
US07135563B2

Reaction notes

Loading…