HCID 56645735, compound → HCID 56645736, compound

HRID 38653Notes

Reaction equation

HRID 38653 reaction equation
[P:1]([O:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]3[O:32][CH2:31][O:30][C:27]=3[CH:28]=2)[N:23]=[C:22]([C:33]2[C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=3[O:36][CH:37]=2)[CH:21]=1)([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2]>CO.[Pd]>[P:1]([OH:11])([OH:3])([O:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]3[O:32][CH2:31][O:30][C:27]=3[CH:28]=2)[N:23]=[C:22]([C:33]2[C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=3[O:36][CH:37]=2)[CH:21]=1)=[O:2]

Participants

4

Reactant 1

HCID 56645735HCID 56645735, compound

Product 1

HCID 56645736HCID 56645736, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 157 (80.1 mg, 0.14 mmol) in anhydrous MeOH (40 mL) was hydrogenated in the presence of 10% Pd/C (40.0 mg) at 25° C. for 15 min. The catalyst and precipitate were collected and dissolved in 10% NaHCO3 solution and then filtered. The filtrate was acidified with dil aq HCl and the precipitate was then collected and washed with acetone to give 158. Obtained as white solid; yield: 46.3%; ESI-MS (Positive mode): m/z 386 [M+H]+, 408 [M+Na]+; ESI-MS (Negative mode): m/z 384 [M−H]−; 1H-NMR (D2O+NaOD, 500 MHz): δ 6.12 (2H, s), 7.32 (1H, s), 7.42 (2H, m), 7.56 (1H, s), 7.63 (1H, d, J=8.0 Hz), 7.78 (1H, s), 8.29 (1H, d, J=7.0 Hz), 8.40 (1H, s).

Workup

  1. customThe catalyst and precipitate were collected
  2. dissolutiondissolved in 10% NaHCO3 solution
  3. filtrationfiltered
  4. customthe precipitate was then collected
  5. washwashed with acetone

Sources & evidence

ORD record
ord-c53fbbcd479841f88297f613a173abdc
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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