Sodium Hydroxide → HCID 15407423, compound

HRID 1274300Notes

Reaction equation

[CH3:1][C:2]1([CH3:23])[CH2:21][C:6]2=[C:7]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[S:8][C:9]([S:10]([CH3:13])(=O)=O)=[C:5]2[C:4](=[O:22])[CH2:3]1.[OH-].[Na+].SC1[S:28][CH:29]=[CH:30][N:31]=1>CCO>[CH3:1][C:2]1([CH3:23])[CH2:21][C:6]2=[C:7]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[S:8][C:9]([S:10][C:13]3[S:28][CH:29]=[CH:30][N:31]=3)=[C:5]2[C:4](=[O:22])[CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 6,6-dimethyl-3-methanesulphonyl-1-(pyrrolidin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (400 mg, 1.1 mmol) in EtOH (10 mL) was added NaOH (1.1 mL of a 3 M solution, 3.3 mmol) followed by 2-mercaptothiazole (0.39 g, 3.3 mmol). The mixture was heated at 70° C. for 5 h then the solution was evaporated. The residue was partitioned between EtOAc (20 mL) and NaOH (1 M; 30 mL). The organic phase was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with EtOAc:hexane (2:1), to afford the title compound (120 mg. 28%) as a colourless solid. 1H NMR (250 MHz, CDCl3) δ 1.07 (6H, s), 1.90-1.95 (4H, m), 2.45 (2H, s), 2.83 (2H, s), 3.40-3.62 (4H, m), 7.55 (1H, d, J=3.4 Hz), 7.97 (1H, d, J=3.4 Hz). MS (ES+) 393 (M+1).

Workup

customthe solution was evaporated
customThe residue was partitioned between EtOAc (20 mL) and NaOH (1 M; 30 mL)
customThe organic phase was separated
dry with materialdried (Na2SO4)
customevaporated
customThe residue was chromatographed on silica gel
washeluting with EtOAc:hexane (2:1)

Sources & evidence

ORD record: ord-52b1ac3940ed4bfd91c4d09a905d38db
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06156787

Reaction notes

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