(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

HRID 1486670Notes

Reaction equation

HRID 1486670 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.[CH3:22][C:23]12[CH2:33][CH:27]3[CH2:28][C:29]([CH3:32])([CH2:31][C:25]([C:34]([O:36][CH:37](Cl)[CH3:38])=[O:35])([CH2:26]3)[CH2:24]1)[CH2:30]2>>[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][CH2:38][CH2:37][O:36][C:34]([C:25]12[CH2:31][C:29]3([CH3:32])[CH2:28][CH:27]([CH2:33][C:23]([CH3:22])([CH2:30]3)[CH2:24]1)[CH2:26]2)=[O:35])=[O:19]

Participants

3

Reactant 2

HCID 117987522(1S,2S,3S,5R,6S)-3'-((allyloxy)carbonyl)-3-fluoro-5'-oxospiro[bicyclo[3.1.0]hexan-2,4'-oxazolidine]-6-carboxylic acidHCID 1179875271-Chloroethyl 3,5-dimethyladamantane-1-carboxylate

Product 1

HCID 117987618(1S,2S,3S,5R,6S)-2-Amino-6-(((3,5-dimethyladamantane-1-carbonyl)oxy)ethoxy)carbonyl-3-fluorobicyclo[3.1.0]hexane-2-carboxylic acidYield 9.6%

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, 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.

Sources & evidence

ORD record
ord-80ca93dbd146404c8ed150b17848b8e3
Source dataset
uspto-grants-2016_08
Patent number
US09428483B2

Reaction notes

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