HCID 14541574, compound → HCID 14541575, compound

HRID 1464022Notes

Reaction equation

HRID 1464022 reaction equation
C([O:8][C:9]([C:11]1[NH:15][C:14]([CH2:16][C:17]2[NH:18][C:19]([CH2:26][C:27]3[NH:28][C:29]([C:39]([O:41]CC4C=CC=CC=4)=[O:40])=[C:30]([CH3:38])[C:31]=3[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:20]([CH2:24][CH3:25])[C:21]=2[CH2:22][CH3:23])=[C:13]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])[C:12]=1[CH3:55])=[O:10])C1C=CC=CC=1>C1COCC1.[Pd]>[C:39]([C:29]1[NH:28][C:27]([CH2:26][C:19]2[NH:18][C:17]([CH2:16][C:14]3[NH:15][C:11]([C:9]([OH:10])=[O:8])=[C:12]([CH3:55])[C:13]=3[CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=[C:21]([CH2:22][CH3:23])[C:20]=2[CH2:24][CH3:25])=[C:31]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:30]=1[CH3:38])([OH:41])=[O:40]

Participants

4

Reactant 1

HCID 14541574HCID 14541574, compound

Product 1

HCID 14541575HCID 14541575, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2,5-Bis(5-benzyloxycarbonyl-3-ethoxycarbonylmethyl-4-methylpyrrol-2-ylmethyl)-3,4-diethylpyrrole (11) (0.75 g, 1 mmol) was dissolved in 85 ml of dry THF and hydrogenated over 10% palladium-charcoal (41 mg) at 1 atm H2 until the reaction was deemed complete as judged by TLC. The catalyst was then separated by filtration, the solvent reduced in volume on the rotary evaporator, and the product precipitated by trituration with n-heptane. The white precipitate was collected by filtration and dried in vacuo to yield 0.56 g (98%) of 12 (m.p. 149° C. (dec.)), which was then used directly in the next step (the synthesis of 3, vide infra) without further purification.

Workup

  1. customThe catalyst was then separated by filtration
  2. customthe solvent reduced in volume on the rotary evaporator
  3. customthe product precipitated by trituration with n-heptane
  4. filtrationThe white precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-be8a23055db14d328620a3fbb3826a8b
Source dataset
uspto-grants-1994_04
Patent number
US05302714

Reaction notes

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