HCID 13817964, compound → N-formyl-(S)-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2oxetanyl]methyl]octadecyl ester

HRID 2106853Notes

Reaction equation

HRID 2106853 reaction equation
[CH2:1]([C@@H:3]1[C:6](=[O:7])[O:5][C@H:4]1[CH2:8][C@@H:9]([O:27][C:28](=[O:45])[C@H:29]([CH2:41][CH:42]([CH3:44])[CH3:43])[NH:30][C:31](OCC1C=CC=CC=1)=[O:32])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:2]>C1COCC1.[Pd]>[CH2:1]([C@@H:3]1[C:6](=[O:7])[O:5][C@H:4]1[CH2:8][C@@H:9]([O:27][C:28](=[O:45])[C@H:29]([CH2:41][CH:42]([CH3:43])[CH3:44])[NH:30][CH:31]=[O:32])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH3:2]

Participants

4

Reactant 1

HCID 13817964HCID 13817964, compound

Product 1

HCID 13817968N-formyl-(S)-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2oxetanyl]methyl]octadecyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

565 mg of N-[(benzyloxy)carbonyl]-L-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2-oxetanyl]methyl]octadecyl ester were dissolved in 12 ml of THF. The mixture was hydrogenated at room temperature in the presence of 40 mg of 10% Pd/C. After the reaction was finished the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in 9 ml of THF and 71 μl of formic acid/acetic acid anhydride were added dropwise. The mixture was diluted with 5 ml of diethyl ether and washed twice with 2% sodium hydrogen carbonate solution and then with water. After drying over sodium sulfate it was filtered and evaporated. By chromatography on silica gel and recrystallization from n-pentane there was obtained N-formyl-(S)-leucine (S)-1-[[(2S,3S)-3-ethyl-4-oxo-2-oxetanyl]methyl]octadecyl ester of m.p. 60°-61° C.

Workup

  1. filtrationwas filtered off
  2. customthe filtrate was evaporated
  3. addition71 μl of formic acid/acetic acid anhydride were added dropwise
  4. additionThe mixture was diluted with 5 ml of diethyl ether
  5. washwashed twice with 2% sodium hydrogen carbonate solution
  6. dry with materialAfter drying over sodium sulfate it
  7. filtrationwas filtered
  8. customevaporated
  9. customBy chromatography on silica gel and recrystallization from n-pentane

Sources & evidence

ORD record
ord-24bbcdfc5ce1406abff78b58ff98252f
Source dataset
uspto-grants-1990_06
Patent number
US04931463

Reaction notes

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