Water → HCID 18442424, compound

HRID 458931Notes

Reaction equation

[CH2:1]([C:5]1([CH2:27][CH2:28][CH2:29][CH3:30])[C:11](=[O:12])[N:10]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:9]2[CH:20]=[C:21]([Br:26])[C:22]([O:24][CH3:25])=[CH:23][C:8]=2[S:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-:32].[K+].[K+].ClC1C=C(C=CC=1)C(OO)=O.C([O-])(O)=O.[Na+].[OH2:53]>C(Cl)Cl>[O:53]=[S:7]1(=[O:32])[C:8]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]([Br:26])=[CH:20][C:9]=2[N:10]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:11](=[O:12])[C:5]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 3,3-dibutyl-4-oxo-5-(4-chlorophenyl)-7-bromo-8-methoxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 95; 0.67 g, 1.304 mmol), DCM (34 ml), water (34 ml) and potassium carbonate (0.554 g, 4.0 mmol) was added at 0° C. m-chloroperoxybenzoic acid (0.78 g, 3.2 mmol) in one portion. The reaction mixture was stirred at 0° C. for 10 h and then at room temperature for 14 hours. DCM (100 ml) and NaHCO3 (aq, sat; 150 ml) were added. The organic layer was separated, washed with brine, dried and evaporated under reduced pressure to give the title compound 0.68 g (96%). NMR (600 MHz) 0.7–0.92 (m, 6H), 1.0–1.60 (m, 10H), 1.70–1.92 (m, 2H), 2.30–3.7 (m, 2H), 3.99 (s, 3H), 7.16–7.20 (m, 2H), 7.24 (s, 1H), 7.34–7.37 (m, 2H), 7.44 (s, 1H); m/z 543.

Workup

waitat room temperature for 14 hours
customThe organic layer was separated
washwashed with brine
customdried
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-0898a08145f545a1b700795cfaeadf41
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192945B2

Reaction notes

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