HCID 86655579, compound → HCID 86655580, compound

HRID 39281Notes

Reaction equation

HRID 39281 reaction equation
C([N:8]([C:20](=[O:50])[CH2:21][C:22]([C:25]1[CH:30]=[C:29]([P:31]([O:42][CH2:43][CH3:44])([CH2:33][P:34]([O:39][CH2:40][CH3:41])([O:36][CH2:37][CH3:38])=[O:35])=[O:32])[CH:28]=[CH:27][C:26]=1[O:45][C:46](=[O:49])[CH2:47][CH3:48])([CH3:24])[CH3:23])[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C1C=CC=CC=1>CO.[Pd]>[C:46]([O:45][C:26]1[CH:27]=[CH:28][C:29]([P:31]([O:42][CH2:43][CH3:44])([CH2:33][P:34]([O:36][CH2:37][CH3:38])([O:39][CH2:40][CH3:41])=[O:35])=[O:32])=[CH:30][C:25]=1[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:50])(=[O:49])[CH2:47][CH3:48]

Participants

4

Reactant 1

HCID 86655579HCID 86655579, compound

Product 1

HCID 86655580HCID 86655580, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 125 (240 mg, 0.329 mmol) was dissolved in methanol (10 mL) and hydrogenated over Pd/C (60 mg, 30%) under H2 (1 atm) for 3 hr. The catalyst was filtered off and the solvent removed under reduced pressure resulting in the pale-yellow liquid 126 (197 mg, 94%): 1H NMR (400 MHz, CDCl3) δ 1.23 (t, J=7.0, 3H), 1.25 (t, J=7.0, 3H), 1.29-1.40 (m, 18H), 1.41 (s, 3H), 1.43 (s, 3H), 1.54 (s, 3H), 1.56 (s, 3H), 2.27 (d, J=12.9, 1H), 2.42 (d, J=12.8, 1H), 2.54-2.90 (m, 12H), 2.96 (d, J=6.2, 1H), 2.99 (d, J=6.3, 1H), 3.89-4.30 (m, 12H), 4.56-4.78 (m, 2H), 5.72 (d, J=8.5, 1H), 5.85 (d, J=8.9, 1H), 7.07 (dd, J=2.1, 3.6, 2H), 7.09 (dd, J=2.1, 3.6, 2H), 7.13-7.24 (m, 10H), 7.58-7.67 (m, 2H), 7.79-7.87 (m, 2H): 31P (162 MHz, CDCl3) δ 22.28 (d, J=5.3, 1P), 22.37 (d, J=1.9, 1 P), 34.38 (d, J=5.3, 1 P), 34.91 (d, J=1.9, 1 P).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3e2974c0d6054a7dbe1ae66ee24a9229
Source dataset
uspto-grants-2013_09
Patent number
US08524691B2

Reaction notes

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