HCID 136403680, compound → HCID 136403632, compound

HRID 494516Notes

Reaction equation

HRID 494516 reaction equation
C([O:8][C:9]1[CH:38]=[CH:37][C:12]2[NH:13][C:14]([C:19]3[C:20](=[O:36])[C:21]([CH3:35])([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[C:22]4[C:27]([C:28]=3[OH:29])=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:15][S:16](=[O:18])(=[O:17])[C:11]=2[CH:10]=1)C1C=CC=CC=1>O1CCCC1.[Pd]>[OH:29][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH3:35])([CH2:30][CH2:31][CH:32]([CH3:33])[CH3:34])[C:20](=[O:36])[C:19]=1[C:14]1[NH:13][C:12]2[CH:37]=[CH:38][C:9]([OH:8])=[CH:10][C:11]=2[S:16](=[O:17])(=[O:18])[N:15]=1

Participants

4

Reactant 1

HCID 136403680HCID 136403680, compound

Product 1

HCID 136403632HCID 136403632, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 28G (1.68 g, 3.17 mmol) in tetrahydrofuran (40 mL) was treated with 10% palladium on carbon (0.168 g, 10% weight) and stirred at 25° C. under a hydrogen balloon for 72 hours. The vessel was purged with nitrogen gas and the mixture was filtered through celite. The filtrate was concentrated in vacuo to give the title compound (1.38 g, 99%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.43 (m, 1 H) 0.74 (m, 7 H) 1.32 (m, 1 H) 1.58 (m, 3 H) 2.15 (m, 2 H) 7.17 (m, 2 H) 7.57 (m, 2 H) 7.76 (m, 2 H) 8.16 (m, 1 H) 10.40 (m, 1 H) 13.66 (m, 1 H). MS (ESI−) m/z 439 (M−H)−.

Workup

  1. customThe vessel was purged with nitrogen gas
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bbde40f7d49e4153b669c9ee51de57b2
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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