Diethylcarbamoyl chloride → HCID 67292039, compound

HRID 1685455Notes

Reaction equation

[C:1]([O:4][C@@H:5]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[CH2:24][S:23][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](B2OC(C)(C)C(C)(C)O2)[CH:13]=1)(=[O:3])[CH3:2].[CH2:35]([N:37]([CH2:41][CH3:42])[C:38](Cl)=[O:39])[CH3:36]>C1COCC1>[C:1]([O:4][C@@H:5]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[CH2:24][S:23][C@H:6]1[O:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:38]([N:37]([CH2:41][CH3:42])[CH2:35][CH3:36])=[O:39])[CH:13]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

1 g (2.02 mM) of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside, 0.5 ml (3.95 mM) of diethylcarbamoyl chloride, 50 mg (0.06 mM) of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) dichloromethane and 15 ml of THF are placed under an argon atmosphere in a reactor adapted for microwaves. The mixture is heated at 110° C. for 30 minutes by microwaves. The cooled reaction mixture is filtered and then concentrated under reduced pressure. The evaporation residue is purified by chromatography on silica gel using pure dichloromethane and then a dichloromethane/methanol mixture (9/1; v/v) as the eluent. After washing with an ether/isopropyl ether mixture, the brown solid obtained is used directly in the deacetylation reaction described in Example 160.

Workup

customThe cooled reaction mixture
filtrationis filtered
concentrationconcentrated under reduced pressure
customThe evaporation residue is purified by chromatography on silica gel using pure dichloromethane
washAfter washing with an ether/isopropyl ether mixture
customthe brown solid obtained
customis used directly in the deacetylation reaction

Sources & evidence

ORD record: ord-1ca1c40471784de5b7526054079ffd67
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148407B2

Reaction notes

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