Trifluoroacetic acid → HCID 22326974, compound

HRID 1602008Notes

Reaction equation

HRID 1602008 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:17])([CH3:16])[CH2:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])(C)C.FC(F)(F)C(O)=O.C(=O)([O-])ON1C(=O)CC(C[C:34]2[C:46]3C[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:38]=3[CH:37]=[CH:36][CH:35]=2)C1=O>ClCCl>[CH:43]1[C:44]2[CH:4]([CH2:1][O:5][C:6]([NH:8][C:9]([CH3:16])([CH3:17])[CH2:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[O:7])[C:46]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:39]=2[CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10847814(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acidHCID 86587341HCID 86587341, compound

Product 1

HCID 22326974HCID 22326974, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2E)-5-(tert-butyloxycarbonylamino)-5-methylhex-2-enoic acid (0.5 g, 2.1 mmol) in dichloromethane (5 ml) was added trifluoroacetic acid (5 ml) and stirred for 60 min and concentrated in vacuo. Then a 10% aqueous solution of sodium carbonate (30 ml) and dioxane (30 ml) were added followed by 9H-fluorenylmethyl-succinimidyl carbonate (0.67 g, 2.1 mmol) and stirred overnight. The mixture was washed with petrol ether (2×20 ml) and the aqueous layer was acidified with 4N sulphoric acid (pH~3) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with 1N sulfuric acid, water (4×20 ml), brine (20 ml), dried (Magnesiumsulfate) and concentrated in vacuo. The obtained product was precipitated from dichloromethane/ether and filtered to give 280 mg of (2E)-5-(((9H-flouren-9-yl)methoxy)carbonylamino)-5-methyl-hex-2-enoic acid, which was used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThen a 10% aqueous solution of sodium carbonate (30 ml) and dioxane (30 ml) were added
  3. stirringstirred overnight
  4. washThe mixture was washed with petrol ether (2×20 ml)
  5. extractionextracted with ethyl acetate (3×50 ml)
  6. washThe combined organic layers were washed with 1N sulfuric acid, water (4×20 ml), brine (20 ml)
  7. dry with materialdried (Magnesiumsulfate)
  8. concentrationconcentrated in vacuo
  9. customThe obtained product was precipitated from dichloromethane/ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-629097c8c26a40d2b874849b94bdf420
Source dataset
uspto-grants-1999_11
Patent number
US05977178

Reaction notes

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