4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one → HCID 72550983, compound

HRID 1486685Notes

Reaction equation

C(OC([NH:7][C@@:8]1([C:18]([OH:20])=[O:19])[C@@H:13]([F:14])[CH2:12][C@@H:11]2[C@H:9]1[C@H:10]2[C:15]([OH:17])=[O:16])=O)C=C.Br[CH2:22][C:23]1[O:24][C:25](=[O:29])[O:26][C:27]=1[CH3:28]>>[NH2:7][C@@:8]1([C:18]([O:20][CH2:22][C:23]2[O:24][C:25](=[O:29])[O:26][C:27]=2[CH3:28])=[O:19])[C@@H:13]([F:14])[CH2:12][C@@H:11]2[C@H:9]1[C@H:10]2[C:15]([O:17][CH2:22][C:23]1[O:24][C:25](=[O:29])[O:26][C:27]=1[CH3:28])=[O:16]

Participants

Reactant 2

HCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

HCID 117987534HCID 117987534, compound

Product 1

HCID 72550983HCID 72550983, compoundYield 29.3%

Procedure

(1S,2S,3S,5R,6S)-2-(((Allyloxy)carbonyl)amino)-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (A-1-1, 660 mg) and 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one (639 mg) were treated in the same manner as in Example A-1 (3) and (4) to give the title compound (C-2, 207 mg) as a pale yellow oil.

Sources & evidence

ORD record: ord-a24b495865cd4f898f17a400170dc5e6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428483B2

Reaction notes

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