Nitrogen → (2S,3S)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

HRID 625894Notes

Reaction equation

HRID 625894 reaction equation
N#N.[N:3]([C@@H:6]([C@H:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:13]=1)[CH3:11])[C:7]([OH:9])=[O:8])=[N+]=[N-]>CO.[Pd]>[NH2:3][C@@H:6]([C@H:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH:13]=1)[CH3:11])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 947NitrogenHCID 11244851(25,35)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

Product 1

HCID 15547324(2S,3S)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

10% Pd on carbon (1.19 g, 1.118 mmol) was placed in a flask under a blanket of N2 (g). The catalyst was wet with MeOH (5 mL). To the flask was added (2S,3S)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid (2.38 g, 6.91 mmol) as a solution in MeOH (69.1 ml). The flask was evacuated then charged with H2 (g). The reaction was stirred for 2 h. The flask was evacuated and purged with N2 (g) 2×. The reaction was filtered through CELITE® and the filter cake washed with MeOH. The organics were concentrated under vacuum to give (2S,3S)-2-amino-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)butanoic acid which was used in Step 7 as is. ESI-MS(+) m/z 319.4 (M+H).

Workup

  1. customThe flask was evacuated
  2. additionthen charged with H2 (g)
  3. customThe flask was evacuated
  4. custompurged with N2 (g) 2×
  5. filtrationThe reaction was filtered through CELITE®
  6. washthe filter cake washed with MeOH
  7. concentrationThe organics were concentrated under vacuum

Sources & evidence

ORD record
ord-a2a8507bc67948d4a229e4842a112036
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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