Benzyl((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-3,13(16),14-trien-11-yl)carbamate → (8S,11R)-11-Amino-8-isopropyl-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-10-one

HRID 626639Notes

Reaction equation

HRID 626639 reaction equation
C(OC(=O)[NH:10][C@@H:11]1[CH2:25][C:24]2=[CH:26][N:21]([CH:22]=[N:23]2)[CH2:20][CH:19]=[CH:18][CH2:17][O:16][CH2:15][C@H:14]([CH:27]([CH3:29])[CH3:28])[NH:13][C:12]1=[O:30])C1C=CC=CC=1>CO.[Pd]>[NH2:10][C@@H:11]1[CH2:25][C:24]2=[CH:26][N:21]([CH:22]=[N:23]2)[CH2:20][CH2:19][CH2:18][CH2:17][O:16][CH2:15][C@H:14]([CH:27]([CH3:28])[CH3:29])[NH:13][C:12]1=[O:30]

Participants

4

Reactant 1

HCID 86655968Benzyl((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-3,13(16),14-trien-11-yl)carbamate

Product 1

HCID 67028858(8S,11R)-11-Amino-8-isopropyl-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-13(16),14-dien-10-oneYield 17.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.49 g (1.14 mmol) of benzyl((8S,11R)-8-isopropyl-10-oxo-6-oxa-1,9,14-triazabicyclo[11.2.1]hexadeca-3,13(16),14-trien-11-yl)carbamate from step C in 80 ml of methanol was hydrogenated over 0.12 g of palladium on carbon (10%) under a hydrogen atmosphere under autogenous pressure at RT. After the starting material had completely reacted, the mixture was filtered and concentrated. The residue was purified by preparative HPLC. 0.06 g of the title compound was obtained.

Workup

  1. customAfter the starting material had completely reacted
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ae2eaccdc314435eaccf95cf2160b291
Source dataset
uspto-grants-2016_04
Patent number
US09309207B2

Reaction notes

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