1-Chloroethyl cyclooctyl carbonate → (1S,2S,3S,5R,6S)-2-Amino-6-((1-(((cyclooctyloxy)carbonyl)oxy)ethoxy)carbonyl)-3-fluorobicyclo[3.1.0]hexane-2-carboxylic acid

HRID 1486678Notes

Reaction equation

C(OC([N:7]1[C@:11]2([C@@H:16]([F:17])[CH2:15][C@@H:14]3[C@H:12]2[C@H:13]3[C:18]([OH:20])=[O:19])[C:10](=[O:21])[O:9]C1)=O)C=C.[C:22](=[O:36])([O:27][CH:28]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[O:23][CH:24](Cl)[CH3:25]>>[NH2:7][C@@:11]1([C:10]([OH:9])=[O:21])[C@@H:16]([F:17])[CH2:15][C@@H:14]2[C@H:12]1[C@H:13]2[C:18]([O:20][CH:24]([O:23][C:22]([O:27][CH:28]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:36])[CH3:25])=[O:19]

Participants

Reactant 2

HCID 1179874961-Chloroethyl cyclooctyl carbonate

HCID 117987522(1S,2S,3S,5R,6S)-3'-((allyloxy)carbonyl)-3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexan-2,4'-oxazolidine]-6-carboxylic acid

Product 1

HCID 117987510(1S,2S,3S,5R,6S)-2-Amino-6-((1-(((cyclooctyloxy)carbonyl)oxy)ethoxy)carbonyl)-3-fluorobicyclo[3.1.0]hexane-2-carboxylic acidYield 18.2%

Procedure

(1S,2S,3S,5R,6S)-3′-((Allyloxy)carbonyl)-3-fluoro-5′-oxospiro[bicyclo[3.1.0]hexan-2,4′-oxazolidine]-6-carboxylic acid (A-1-2, 380 mg) and 1-chloroethyl cyclooctyl carbonate (A-11-1, 745 mg) were treated in the same manner as in Example A-1 (3) and (4) to give the title compound (A-11, 93 mg) as a colorless solid.

Sources & evidence

ORD record: ord-f96ab0f2b1aa408f80a1bece423eded7
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428483B2

Reaction notes

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