Lithium Hydroxide → 7'-Bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9'-xanthen]-2-amine

HRID 455616Notes

Reaction equation

[OH-].[Li+].[Br:3][C:4]1[CH:17]=[C:16]2[C:7]([O:8][C:9]3[C:10]([F:34])=[CH:11][C:12]([O:32][CH3:33])=[CH:13][C:14]=3[C:15]32[CH2:22][CH2:21][S:20][C:19]([NH:23]C(=O)C2C=CC=CC=2)=[N:18]3)=[CH:6][CH:5]=1>CO.O>[Br:3][C:4]1[CH:17]=[C:16]2[C:7]([O:8][C:9]3[C:10]([F:34])=[CH:11][C:12]([O:32][CH3:33])=[CH:13][C:14]=3[C:15]32[CH2:22][CH2:21][S:20][C:19]([NH2:23])=[N:18]3)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A 2 N solution of lithium hydroxide (22.50 ml, 45.0 mmol) was added to a solution of N-(7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2-yl)benzamide (7.7 g, 15.00 mmol) in MeOH (250 ml). The reaction mixture was heated to 65° C. for 3 hours. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic extracts were concentrated under reduced pressure. The residue was purified via column chromatography [0-70% 90/10/1 (DCM/MeOH/ammonia) in DCM] to afford 7′-bromo-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2-amine as a racemic mixture (2 g, 2.443 mmol, 32% yield).

Workup

extractionextracted with EtOAc
concentrationThe combined organic extracts were concentrated under reduced pressure
customThe residue was purified via column chromatography [0-70% 90/10/1 (DCM/MeOH/ammonia) in DCM]

Sources & evidence

ORD record: ord-2f1c965b5b1f42ca8ca7362137b9aad6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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