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 2274548Notes

Reaction equation

HRID 2274548 reaction equation
[CH:1]([C@@H:4]1[NH:18][C:17](=[O:19])[C@H:16]([NH:20]C(=O)OCC2C=CC=CC=2)[CH2:15][C:14]2=[CH:31][N:11]([CH:12]=[N:13]2)[CH2:10][CH:9]=[CH:8][CH2:7][O:6][CH2:5]1)([CH3:3])[CH3:2]>CO.[Pd]>[NH2:20][C@@H:16]1[CH2:15][C:14]2=[CH:31][N:11]([CH:12]=[N:13]2)[CH2:10][CH2:9][CH2:8][CH2:7][O:6][CH2:5][C@H:4]([CH:1]([CH3:2])[CH3:3])[NH:18][C:17]1=[O:19]

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-568fa15a8d0546048e68575d025f4e31
Source dataset
uspto-grants-2015_09
Patent number
US09126955B2

Reaction notes

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