HCID 131713059, compound → HCID 131713058, compound

HRID 435392Notes

Reaction equation

HRID 435392 reaction equation
[NH:1]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([N:17]1[CH2:31][CH2:30][CH2:29][C@H:18]1[C:19]([O:21]CC1C=CC=CC=1)=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]>C(O)CCC.C(O)C.[Pd]>[NH:1]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([N:17]1[CH2:31][CH2:30][CH2:29][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

5

Reactant 1

HCID 131713059HCID 131713059, compound

Product 1

HCID 131713058HCID 131713058, compoundYield 94.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 2631-ButanolSolventHCID 702EthanolSolvent

Procedure

Substance [2] (76.98 g, 145 mM) was dissolved in n-butanol (20 ml) and ethanol (300 ml). 5% Pd/C (15 g) was added thereto and catalytic hydrogenation was allowed to proceed for 3 hours. After removing the catalyst, the mother liquor was concentrated in vacuo. Diethyl ether (300 ml) was added to the residue, which was then extracted successively with 500 ml and 200 ml of 5% aqueous sodium bicarbonate. The extract was adjusted to pH 4 by adding 1 N HCl with ice cooling to precipitate the product continuously, which was extracted with ethyl acetate and washed twice with water. After drying with anhydrous sodium sulfate, the solution was concentrated in vacuo. The residue was solidified by adding ether-hexane. Recrystallization was effected with ethyl acetate-ether-hexane to obtain the substance [3] (60.33 g, yield: 94.2%).

Workup

  1. customAfter removing the catalyst
  2. concentrationthe mother liquor was concentrated in vacuo
  3. additionDiethyl ether (300 ml) was added to the residue, which
  4. extractionwas then extracted successively with 500 ml and 200 ml of 5% aqueous sodium bicarbonate
  5. additionby adding 1 N HCl with ice cooling
  6. customto precipitate the product continuously
  7. extractionwhich was extracted with ethyl acetate
  8. washwashed twice with water
  9. dry with materialAfter drying with anhydrous sodium sulfate
  10. concentrationthe solution was concentrated in vacuo
  11. additionby adding ether-hexane
  12. customRecrystallization

Sources & evidence

ORD record
ord-18dc2d6073fd444a9359f472ad67e2b4
Source dataset
uspto-grants-1983_08
Patent number
US04400316

Reaction notes

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