Chloromethyl octanoate → (1S,2S,3S,5R,6S)-2-amino-3-fluoro-6-(((octanoyloxy)methoxy)carbonyl)bicyclo[3.1.0]hexane-2-carboxylic acid

HRID 1486671Notes

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:31][CH2:32]Cl)(=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>>[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][CH2:32][O:31][C:22](=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:19]

Participants

Reactant 2

HCID 525231Chloromethyl octanoate

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 72550320(1S,2S,3S,5R,6S)-2-amino-3-fluoro-6-(((octanoyloxy)methoxy)carbonyl)bicyclo[3.1.0]hexane-2-carboxylic acidYield 26.4%

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, 300 mg) and chloromethyl octanoate (483 mg) were treated in the same manner as in Example A-1 (3) and (4) to give the title compound (A-6, 95 mg) as a colorless solid.

Sources & evidence

ORD record: ord-2a4e2cc54f6a48d4939197f08ca4b036
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428483B2

Reaction notes

Loading…