HCID 86708054, compound → HCID 86708055, compound

HRID 1524352Notes

Reaction equation

HRID 1524352 reaction equation
C(OC(=O)[N:10]([C@@H:16]([CH2:36][CH2:37][CH:38]([F:62])[CH2:39][NH:40][C:41](=[O:61])[C@H:42]([CH:48]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[NH:43][C:44]([O:46][CH3:47])=[O:45])[CH2:17][O:18][Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])C1C=CC=CC=1>CO.[Pd]>[Si:19]([O:18][CH2:17][C@@H:16]([NH:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:36][CH2:37][CH:38]([F:62])[CH2:39][NH:40][C:41](=[O:61])[C@H:42]([CH:48]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[NH:43][C:44]([O:46][CH3:47])=[O:45])([C:32]([CH3:33])([CH3:34])[CH3:35])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 86708054HCID 86708054, compound

Product 1

HCID 86708055HCID 86708055, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the material from Step 11 (110 mg, 0.126 mmol) in methanol (1 mL) was degassed with nitrogen, then 10% Pd/C (14 mg, 0.013 mmol) was added. The reaction mixture was stirred under hydrogen (1 atm) for 3 hours. The mixture was filtered through celite and washed with dichloromethane. The filtrate was concentrated in vacuo to afford 86 mg of the title compound which was used directly at Step 13. LCMS (M+1)=740

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-882a26c34cae4874b92d2a88f0ec74bf
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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