Sodium Hydroxide → HCID 11606047, compound

HRID 2425091Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]([CH3:31])[C:10]2[O:16][C:15]3[C:17]([Cl:27])=[CH:18][C:19]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[CH:20][C:14]=3[CH2:13][S:12](=[O:29])(=[O:28])[C:11]=2[CH:30]=1)=[O:6]>O.O1CCCC1>[Cl:27][C:17]1[C:15]2[O:16][C:10]3[C:9]([CH3:31])=[CH:8][C:7]([C:5]([OH:6])=[O:4])=[CH:30][C:11]=3[S:12](=[O:28])(=[O:29])[CH2:13][C:14]=2[CH:20]=[C:19]([N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[CH:18]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of sodium hydroxide (0.22 g, 5.49 mmol) in water (15 mL) was added to a solution of 4-chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester (free base of example 16, 0.88 g, 1.83 mmol) in tetrahydrofuran (25 mL). The reaction mixture was stirred at 40° C. for 4 h, the solvent was removed under vacuum. The reaction mixture was acidified to pH 4-5 using 10% aqueous hydrochloric acid. The precipitate was filtered, washed with water and dried to obtain the title compound. Yield: 0.84 g, (98%); 1H NMR (DMSO-d6, 300 MHz): δ 2.65 (s, 3H, CH3), 3.26 (s, 4H, 2CH2), 3.43 (s, 4H, 2CH2), 5.16 (s, 2H, CH2), 7.20 (s, 2H, Ar), 8.08 (s, 1H, Ar), 8.18 (s, 1H, Ar); MS: m/e (ES−) 421 (M−1); analysis: C19H19ClN2O5S.2H2O requires C, 49.73; H, 5.05; N, 6.10; Cl, 7.73; S, 6.99. found: C, 50.27; H, 5.12; N, 6.12; Cl, 7.47; S, 6.92%.

Workup

customthe solvent was removed under vacuum
filtrationThe precipitate was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-b70ce7927e4b494d987a236cc8e3e76e
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964631B2

Reaction notes

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