HCID 86715370, compound → HCID 86715369, compound

HRID 630624Notes

Reaction equation

HRID 630624 reaction equation
[CH2:1]([C@@H:8]([C:39](=[O:76])[NH:40][C@@H:41]([CH2:72][CH:73]([CH3:75])[CH3:74])[C:42](=[O:71])[C@@:43]([OH:70])([CH3:69])[CH2:44][O:45][S:46]([C:49]1[C:66]([CH3:67])=[CH:65][C:52]([O:53][CH2:54][C:55]([O:57]CC2C=CC=CC=2)=[O:56])=[CH:51][C:50]=1[CH3:68])(=[O:48])=[O:47])[NH:9][C:10](=[O:38])[C@H:11]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH:12][C:13](=[O:33])[C@H:14]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:15][C:16](=[O:24])[CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.[Pd]>[CH2:1]([C@@H:8]([C:39](=[O:76])[NH:40][C@@H:41]([CH2:72][CH:73]([CH3:75])[CH3:74])[C:42](=[O:71])[C:43]([OH:70])([CH3:69])[CH2:44][O:45][S:46]([C:49]1[C:66]([CH3:67])=[CH:65][C:52]([O:53][CH2:54][C:55]([OH:57])=[O:56])=[CH:51][C:50]=1[CH3:68])(=[O:48])=[O:47])[NH:9][C:10](=[O:38])[C@H:11]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH:12][C:13](=[O:33])[C@H:14]([CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[NH:15][C:16](=[O:24])[CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86715370HCID 86715370, compound

Product 1

HCID 86715369HCID 86715369, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Referring to FIG. 37, benzyl 2-(4-((((4S,7S,10S,13S,15R)-10-benzyl-15-hydroxy-7,13-diisobutyl-15-methyl-1-morpholino-2,5,8,11,14-pentaoxo-4-phenethyl-3,6,9,12-tetraazahexadecan-16-yl)oxy)sulfonyl)-3,5-dimethylphenoxy)acetate (110 mg, 0.1 mmol) was dissolved in dioxane (10 mL) and Pd/C (50 mg) was added. The mixture was stirred for 3 h under H2 atmosphere (15 psi). The catalyst was filtered off and the filtrate was concentrated under reduced pressure to give compound (100 mg, quantitative); 1H NMR (DMSO-d6, 300 MHz): δ 8.12-8.02 (m, 3H), 7.99-7.89 (m, 1H), 7.32-7.02 (m, 10H), 6.88 (s, 2H), 6.05 (s, 1H), 5.11-5.02 (m, 1H), 5.75 (s, 2H), 4.61-4.22 (m, 4H), 3.65 (m, 4H), 2.95 (m, 2H), 2.78-2.70 (m, 1H), 2.55 (s, 6H), 2.45 (m, 4H), 1.94-1.55 (m, 4H), 0.92-0.74 (m, 12H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give compound (100 mg, quantitative)

Sources & evidence

ORD record
ord-a394622ffd884127a2139426ec3b37f9
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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