Acetic Acid → Sorbinil

HRID 1583469Notes

Reaction equation

C[C@H]([NH2+]C)[C@H](O)C1C=CC=CC=1.[F:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[O:20][CH2:19][CH2:18][C@@:17]2([NH:27][C:28]([NH2:30])=[O:29])[C:24](O)=[O:25].C(O)(=O)C.CO>C(O)C>[F:13][C:14]1[CH:15]=[C:16]2[C@:17]3([C:24](=[O:25])[NH:30][C:28](=[O:29])[NH:27]3)[CH2:18][CH2:19][O:20][C:21]2=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 9.6 g of the (1R,2S)-ephedrine salt of (S)-6-fluoro-4-ureidochroman-4-carboxylic acid and 68 ml of glacial acetic acid was heated at 95° C. for 1 hour, and then it was evaporated in vacuo at 60° C. This afforded 20 g of an oily residue which was diluted with 50 ml of water at 60° C. and then 50 ml of water at 10° C. The resulting slurry was adjusted to pH 4.5 with 4N sodium hydroxide and the solid was recovered by filtration to give 4.7 g of crude title product, mp 234°-240° C., [alpha]D25 =+50.5° (c=1, methanol). This crude product (4.0 g) was dissolved in 60 ml of boiling absolute ethanol, and the ethanol solution was filtered and cooled to 24° C. The solid was recovered by filtration, to give 2.0 g of (S)(+)-6-fluoro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione, mp 240.5-243.0, [alpha]D25 =+55.4° (c=1, methanol).

Workup

customit was evaporated in vacuo at 60° C
additionThis afforded 20 g of an oily residue which was diluted with 50 ml of water at 60° C.
customat 10° C
filtrationthe solid was recovered by filtration
customto give 4.7 g of crude title product, mp 234°-240° C.
filtrationthe ethanol solution was filtered
temperaturecooled to 24° C
filtrationThe solid was recovered by filtration

Sources & evidence

ORD record: ord-36c574f0fe5b4aa3b6fefba5312894e9
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551542

Reaction notes

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