Triphenylphosphine → HCID 22182456, compound

HRID 1796806Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH:19]([C:26]23[O:33][CH2:32][C:29]([CH3:34])([CH2:30][O:31]2)[CH2:28][O:27]3)[CH:20]([NH:22][CH2:23][CH2:24]O)[CH3:21])(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:24][CH2:23][NH:22][CH:20]([CH3:21])[CH:19]2[C:26]23[O:31][CH2:30][C:29]([CH3:34])([CH2:32][O:33]2)[CH2:28][O:27]3)(=[O:16])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Benzyloxy-N-[2-(2-hydroxy-ethylamino)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-propyl]-benzenesulfonamide (compound of formula XLIV, 10.6 g, 21.5 mmol) was diluted with tetrahydrofuran (400 ml) and cooled to about 0° C. prior to the addition of triphenylphosphine (6.69 g, 25.5 mmol) and diethylazodicarboxylate (4.2 ml, 26.7 mmol). The mixture was allowed to stir at about 0° C. for about 2 hours then was concentrated in vacuo and diluted with ethyl acetate and extracted with water. The organic layer was dried with sodium sulfate and concentrated in vacuo. Silica gel chromatography using ethyl acetate followed by 10% methanol in chloroform containing 0.1% ammonium hydroxide gave 6.8 g of a compound of formula XLV.

Workup

concentrationthen was concentrated in vacuo
additiondiluted with ethyl acetate
extractionextracted with water
dry with materialThe organic layer was dried with sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9316c28a923943b59f2d84594da95ce0
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030242B2

Reaction notes

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