Benzylamine → HCID 67292379, compound

HRID 1685418Notes

Reaction equation

C([O:4][C@@H:5]1[C@@H:18]([O:19]C(=O)C)[C@H:17]([O:23]C(=O)C)[CH2:16][S:15][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](Br)[CH:13]=1)(=O)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.N12CCCN=C1CCCCC2.C1C[O:49][CH2:48]C1>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[O:7]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:48]([NH:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:49])[CH:13]=1)[C@@H:6]1[S:15][CH2:16][C@@H:17]([OH:23])[C@H:18]([OH:19])[C@H:5]1[OH:4]

Participants

Conditions

Temperature: 150 °C

Procedure

0.5 g (1.115 mM) of 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylo-pyranoside, 0.37 ml (3.346 mM) of benzylamine, 0.294 g (1.115 mM) of molybdenum hexacarbonyl, 0.042 g (0.056 mM) of Herrmann's catalyst and 0.5 ml (3.346 mM) of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) are mixed in 3 ml of THF. The mixture is heated at 150° C. for 15 minutes by microwaves. The reaction mixture is filtered, the filtrate is taken up in 20 ml of ethyl acetate and the organic phase is washed with 1 N sodium hydroxide solution, dried over magnesium sulfate and concentrated under reduced pressure to give the expected product in the form of a pale yellow solid with a yield of 0.7%.

Workup

filtrationThe reaction mixture is filtered
washthe organic phase is washed with 1 N sodium hydroxide solution
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f4702bcffe8f48f6ae3aa52d4b8af9fc
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148407B2

Reaction notes

Loading…