HCID 56645733, compound → HCID 56645734, compound

HRID 38650Notes

Reaction equation

HRID 38650 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:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][CH:34]=2)[CH:21]=1)([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2]>CO.[Pd]>[P:1]([OH:3])([OH:11])([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:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][CH:34]=2)[CH:21]=1)=[O:2]

Participants

4

Reactant 1

HCID 56645733HCID 56645733, compound

Product 1

HCID 56645734HCID 56645734, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 152 (894.8 mg, 1.55 mmol) in anhydrous MeOH (40 mL) was hydrogenated in the presence of 10% Pd/C (456.7 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 153. Yellow solid; yield: 94.1%; ESI-MS (Negative mode): m/z 394 [M−H]−; 1H-NMR (D2O+NaOD, 500 MHz): δ 6.13 (2H, s), 7.26 (1H, s), 7.50 (1H, ddd, J=8.23, 7.33, 1.20 Hz), 7.55-7.58 (2H, m), 7.62-7.70 (3H, m), 7.98 (1H, d, J=8.53 Hz), 8.02 (1H, d, J=8.96 Hz); 13C-NMR (D2O+NaOD, 125 MHz): δ 98.65, 102.15, 103.54, 109.80, 110.00, 118.35, 125.66, 126.37, 126.84, 127.40, 128.34, 128.97, 130.89, 133.50, 138.15, 146.58, 147.34, 151.27, 158.15, 158.23.

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-19a419b64ce94391bb3c69b7387474db
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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