Diazomethane → HCID 57857030, compound

HRID 561743Notes

Reaction equation

[S:1]1[C:5]([C@H:6]([O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)/[CH:7]=[CH:8]/[C@H:9]2[C@H:13]([OH:14])[CH2:12][C@H:11]([OH:15])[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][C:3]2[CH:43]=[CH:44][CH:45]=[CH:46][C:2]1=2.[N+](=[CH2:49])=[N-]>C(OCC)C>[S:1]1[C:5]([C@H:6]([O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)/[CH:7]=[CH:8]/[C@H:9]2[C@H:13]([OH:14])[CH2:12][C@H:11]([OH:15])[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:49])=[O:23])=[CH:4][C:3]2[CH:43]=[CH:44][CH:45]=[CH:46][C:2]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

(Z)-7-((1R,2R,3R,5S)-2-((R,E)-3-(Benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-3,5-dihydroxycyclopentyl)hept-5-enoic acid, 9a, is dissolved in diethyl ether (0.1 M) and cooled to 0° C. under a nitrogen atmosphere. Diazomethane (freshly prepared solution in diethyl ether) is added to the solution with stirring under a light yellow color persisting. The completion of the reaction is confirmed by the absence of starting material as judged by TLC. Upon completion, the solvents are evaporated and the product is purified by flash chromatography using hexanes-ethyl acetate as eluent to afford the title intermediate 10a.

Workup

customUpon completion, the solvents are evaporated
customthe product is purified by flash chromatography

Sources & evidence

ORD record: ord-e141ad091b3240339c9ea2596e58a680
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063240B2

Reaction notes

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