Triphenylphosphine → HCID 178452578, compound

HRID 1036418

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)[CH:6]=[CH:5]2.[CH2:28]([O:35][CH2:36][C@@H:37]1[CH2:40][C@H:39](O)[CH2:38]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:23]([O:22][C:21](=[O:27])[NH:20][C:12]1([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([O:1][C@H:39]4[CH2:38][C@H:37]([CH2:36][O:35][CH2:28][C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[CH2:40]4)[CH:3]=3)[CH:8]=2)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of [5-(6-Hydroxynaphthalen-2-yl)-2,2-dimethyl-1,3-dioxinan-5-yl]-carbamic acid tert-butyl ester (Example 13, 30.0 mg, 0.0000723 mol), cis-3-benzyloxymethyl-cyclobutanol (13.9 mg, 0.0000723 mol), and triphenylphosphine (22.8 mg, 0.0000868 mol) in THF (2 mL), a solution of diisopropyl azodicarboxylate (18.7 mg, 0.0000868 mol) in THF (1 mL), was added dropwise at 23° C. The reaction mixture was then allowed to stir at 23° C. for 2 days. Solvent was removed, and the crude mixture was purified via chromatography (SiO2, 4 g, ethyl acetate 0-35%) to give a pure product (18 mg, 45%). MS (ES, M−113): 434.30.

Workup

customSolvent was removed
customthe crude mixture was purified via chromatography (SiO2, 4 g, ethyl acetate 0-35%)

Sources & evidence

ORD record: ord-e8f0ae715e4043e89a05e434e4d13734
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546359B2

Linked notes

Loading…