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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1486670Generated: November 1, 2026

(1S,2S,3S,5R,6S)-3'-((allyloxy)carbonyl)-3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexan-2,4'-oxazolidine]-6-carboxylic acid → (1S,2S,3S,5R,6S)-2-Amino-6-(((3,5-dimethyladamantane-1-carbonyl)oxy)ethoxy)carbonyl-3-fluorobicyclo[3.1.0]hexane-2-carboxylic acid

https://huagongshe.com/reaction/1486670

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(1S,2S,3S,5R,6S)-3'-((allyloxy)carbonyl)-3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexan-2,4'-oxazolidine]-6-carboxylic acidHCID 117987522—
Reactant1-Chloroethyl 3,5-dimethyladamantane-1-carboxylateHCID 117987527—
Product(1S,2S,3S,5R,6S)-2-Amino-6-(((3,5-dimethyladamantane-1-carbonyl)oxy)ethoxy)carbonyl-3-fluorobicyclo[3.1.0]hexane-2-carboxylic acidHCID 1179876189.6%

Reaction Steps

(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, 500 mg) and 1-chloroethyl 3,5-dimethyladamantane-1-carboxylate (A-5-1, 1.13 g) were treated in the same manner as in Example A-1 (3) and (4) to give the title compound (A-5, 70 mg) as a colorless solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09428483B2
Source datasetuspto-grants-2016_08
ORD IDord-80ca93dbd146404c8ed150b17848b8e3
Source noteuspto-grants-2016_08