HCID 86708057, compound → HCID 68044413, compound

HRID 1524355Notes

Reaction equation

HRID 1524355 reaction equation
[F:1][CH:2]([CH2:26][CH2:27][C@H:28]([N:31]([CH2:44][CH2:45][CH:46]([CH3:48])[CH3:47])[S:32]([C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-])=O)=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH2:29][OH:30])[CH2:3][NH:4][C:5](=[O:25])[C@H:6]([CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[NH:7][C:8]([O:10][CH3:11])=[O:9]>C(OCC)(=O)C.C(O)C.[OH-].[OH-].[Pd+2]>[NH2:41][C:38]1[CH:37]=[CH:36][C:35]([S:32]([N:31]([CH2:44][CH2:45][CH:46]([CH3:48])[CH3:47])[C@H:28]([CH2:29][OH:30])[CH2:27][CH2:26][CH:2]([F:1])[CH2:3][NH:4][C:5](=[O:25])[C@H:6]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:7][C:8]([O:10][CH3:11])=[O:9])(=[O:33])=[O:34])=[CH:40][CH:39]=1

Participants

4

Reactant 1

HCID 86708057HCID 86708057, compound

Product 1

HCID 68044413HCID 68044413, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of the material from Step 14 (45 mg, 0.065 mmol) in (1:1) in ethyl acetate-ethanol (1 mL) was degassed with nitrogen, then 20% palladium hydroxide on carbon (4.6 mg, 0.007 mmol) was added. The reaction mixture was stirred under hydrogen (1 atm) for 3 hours. The reaction mixture was filtered through celite and washed with dichloromethane to afford 30 mg of the title compound. 1H NMR (DMSO-d6): δ 8.17 (d, J=6.98 Hz, 1H), 7.46-7.38 (m, 3H), 7.35-7.22 (m, 6H), 7.23-7.10 (m, 4H), 6.60 (dd, J=8.50, 3.17 Hz, 2H), 5.94 (s, 2H), 5.03-4.94 (m, 1H), 4.71-4.64 (m, 1H), 4.26 (d, J=11.45 Hz, 1H), 3.94-3.66 (m, 1H), 3.55-3.39 (m, 1H), 3.42 (s, 3H), 3.29-3.22 (m, 2H), 3.13-2.77 (m, 4H), 1.67-1.01 (m, 7H), 0.84 (dd, J=6.31, 3.38 Hz, 6H). The mixture of diastereomers was separated by SFC (AD-H, 4.6×250 mm, 30% i-PrOH in CO2, 2.4 mL/min, 100 bar, 40° C.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-04fc4c8131de46c8840ec55583c48b2d
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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