Sodium Methoxide → HCID 5748291, compound
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:28][CH2:27][CH2:26][C@:8]3([C:12](=[O:13])[NH:11][C:10](=[O:14])[N:9]3C(=O)N[C@@H](C3C=CC=CC=3)C)[C:6]=2[CH:7]=1.C[O-].[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:28][CH2:27][CH2:26][C@:8]3([C:12](=[O:13])[NH:11][C:10](=[O:14])[NH:9]3)[C:6]=2[CH:7]=1Participants
Procedure
In like manner, when pure (4R)-6-fluoro-2,3dihydro-3'-[(R)-1-phenylethylcarbamoyl]spiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5'-dione [the (R) (R)-diastereomer product of Example 1] and sodium methoxide were reacted together in accordance with this same procedure (using the same molar proportions as before), there was eventually obtained (after work-up) a 36% yield of pure (4R)-(-)-6-fluoro-2,3-dihydro-spiro-[4H-1-benzopyran-4,4'-imidazolidine]2',5'-dione in the form of a white crystalline solid melting at 235°-237° C.; [α]D25° -54.1° (c=1 in methanol). This product was also substantially identical in every respect with the corresponding final product first reported as 1-6-fluoro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione m.p. 241°-243° C.; [α]D25° -54.8° (c=1 in methanol)] by R. Sarges in Example I of U.S. Pat. No. 4,130,174.
Sources & evidence
- ORD record
- ord-467a6af2ee2f4ff88801df37ea987738
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05006657
Reaction notes
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