1-Chloroethyl 1-methylethyl carbonate → HCID 117987606, compound

HRID 1486679Notes

Reaction equation

[CH2:1]([O:4][C:5]([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][CH2:8]1)=[O:6])[CH:2]=[CH2:3].[C:22](=[O:31])([O:27][CH:28]([CH3:30])[CH3:29])[O:23][CH:24](Cl)[CH3:25]>>[F:17][C@@H:16]1[C@@:11]2([C:10](=[O:21])[O:9][CH2:8][N:7]2[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH:12]2[C@H:14]([C@@H:13]2[C:18]([O:20][C@@H:24]([O:23][C:22]([O:27][CH:28]([CH3:30])[CH3:29])=[O:31])[CH3:25])=[O:19])[CH2:15]1

Participants

Reactant 2

HCID 117895851-Chloroethyl 1-methylethyl 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 117987606HCID 117987606, compoundYield 18.1%

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, 400 mg) and 1-chloroethyl isopropyl carbonate (204 mg) were treated in the same manner as in Example A-1 (3) to give (1S,2S,3S,5R,6S)-3′-allyl 6-(1-((isopropyloxycarbonyl)oxy)ethyl) 3-fluoro-5′-oxospiro[bicyclo[3.1.0]hexan-2,4′-oxazolidine]-3′,6-dicarboxylate (A-15-1, 95 mg) as a colorless oil.

Sources & evidence

ORD record: ord-991a773bca734b61bd807f3d89f45819
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428483B2

Reaction notes

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