HCID 86725123, compound → HCID 86725122, compound

HRID 1470902Notes

Reaction equation

HRID 1470902 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:17]([C:53]([NH:55][C@H:56]([CH2:67][OH:68])[C:57]([O:59]CC2C=CC=CC=2)=[O:58])=[O:54])=[N:18][C:19]([NH:38][CH2:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH3:52])=[C:20]([C:22]([NH:24][C@H:25]([CH2:36][OH:37])[C:26](=[O:35])[O:27]CC2C=CC=CC=2)=[O:23])[N:21]=1>C(O)C.O.O.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:17]([C:53]([NH:55][C@@H:56]([C:57]([OH:59])=[O:58])[CH2:67][OH:68])=[O:54])=[N:18][C:19]([NH:38][CH2:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][O:51][CH3:52])=[C:20]([C:22]([NH:24][C@@H:25]([C:26]([OH:35])=[O:27])[CH2:36][OH:37])=[O:23])[N:21]=1

Participants

5

Reactant 1

HCID 86725123HCID 86725123, compound

Product 1

HCID 86725122HCID 86725122, compoundYield 26.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A 50 mL round-bottom flask equipped with magnetic stir bar was charged with bis-benzyl ester 12 (0.501 g, 0.521 mmol), dissolved in EtOH—H2O (20 mL; 3:1, v/v), and 10% Pd—C (100 mg) was added as slurry in water (1-2 mL). The reaction mixture was purged thoroughly with argon and then with H2 and stirred at room temperature for 2 h in an atmosphere of H2. The catalyst was removed by filtration, solvents were removed in vacuo, and the crude product subjected to purification by preparative RP-HPLC to give 11 (0.108 g, 26%).

Workup

  1. customA 50 mL round-bottom flask equipped with magnetic stir bar
  2. customThe reaction mixture was purged thoroughly with argon
  3. customThe catalyst was removed by filtration, solvents
  4. customwere removed in vacuo
  5. customthe crude product subjected to purification by preparative RP-HPLC

Sources & evidence

ORD record
ord-1be6230c3e7a4123818a1ae14a0fb2c7
Source dataset
uspto-grants-2015_04
Patent number
US09005581B2

Reaction notes

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