HCID 86726359, compound → HCID 86726360, compound

HRID 629757Notes

Reaction equation

HRID 629757 reaction equation
[N:1]([C@@H:4]([C@@H:40]([C:49]1[CH:54]=[CH:53][C:52]([F:55])=[CH:51][CH:50]=1)[C:41]1[CH:46]=[C:45]([F:47])[CH:44]=[C:43]([F:48])[CH:42]=1)[C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:39])[C:13]=1[CH2:14][CH2:15][C@H:16]1[O:21][CH2:20][C@H:19]([CH2:22][O:23][C:24]([NH:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[O:25])[N:18]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:17]1)=[O:6])=[N+]=[N-].[H][H]>CO.[Pd]>[NH2:1][C@@H:4]([C@@H:40]([C:49]1[CH:54]=[CH:53][C:52]([F:55])=[CH:51][CH:50]=1)[C:41]1[CH:42]=[C:43]([F:48])[CH:44]=[C:45]([F:47])[CH:46]=1)[C:5]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:39])[C:13]=1[CH2:14][CH2:15][C@H:16]1[O:21][CH2:20][C@H:19]([CH2:22][O:23][C:24]([NH:26][CH2:27][C:28]([F:31])([F:29])[F:30])=[O:25])[N:18]([C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:17]1)=[O:6]

Participants

5

Reactant 2

HCID 86726359HCID 86726359, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86726360HCID 86726360, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (2S,3S)-2-azido-3-(4-fluorophenyl)-3-(3,5-difluorophenyl)-N-(5-fluoro-4-(2-((2R,5R)-4-(tert-butyloxycarbonyl)-5-(2,2,2-trifluoroethylaminocarbonyloxymethyl)morpholine-2-yl)ethyl)pyridin-3-yl)propanamide (36 mg, 0.046 mmol) in 1 mL of MeOH was purged with nitrogen gas for 1 min. To the solution was added 10% palladium on carbon (18 mg) and the mixture was stirred under 1 atmosphere of hydrogen gas for 4 h. The catalyst was removed by filtration and the filtrate solvents were removed in vacuo to give a gum. LC MS: RT=1.20 min, M+H=758 (2 min gradient)

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate solvents were removed in vacuo
  3. customto give a gum
  4. customRT=1.20 min, M+H=758 (2 min gradient)

Sources & evidence

ORD record
ord-f14291ca7e1449319dd38d621339e291
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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