Lithium hydroxide, monohydrate → HCID 178490977, compound

HRID 2042736Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([C@H:23]2[CH2:28][CH2:27][C@H:26]([CH2:29][C:30]([O:32]CC)=[O:31])[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)=O.O.[OH-].[Li+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2[S:11][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C@H:23]4[CH2:28][CH2:27][C@H:26]([CH2:29][C:30]([OH:32])=[O:31])[CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[N:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-(3-Methoxyphenyl)-2-thiourea (0.01 g, 0.054 mmol) was added to a solution of the product from Example 48A (0.02 g, 0.054 mmol) in ethanol (0.5 mL) and heated at 80° C. for 1 h. The solvent was then removed in vacuo and the residue taken up in tetrahydrofuran (1 mL) and water (0.5 mL). Lithium hydroxide monohydrate (0.005 g, 0.1 mmol) was added to the reaction mixture and stirred at 50° C. for 3 h. The solvents were then removed and the residue purified by RP-HPLC to afford the title compound as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.09-1.18 (m, 2 H), 1.45-1.54 (m, 2 H), 1.62-1.69 (m, 1 H), 1.70-1.77 (m, 1 H), 1.80-1.88 (m, 4 H), 2.13 (d, J=7 Hz, 2 H), 3.78 (s, 3 H), 6.54 (dd, J=8.24, 1.83 Hz, 1 H), 7.10-7.16 (m, 1 H), 7.20-7.27 (m, 1 H), 7.29 (d, J=8.24 Hz, 2 H), 7.51-7.56 (m, 1 H), 7.79-7.83 (d, J=8.24 Hz, 2 H), 10.25 (s, 1 H), 1.2.05 (s, 1 H): MS (ESI) m/e 423.2 (M+H).

Workup

customThe solvent was then removed in vacuo
customThe solvents were then removed
customthe residue purified by RP-HPLC

Sources & evidence

ORD record: ord-b10dfa9f8c2443d297edbb0362bb9808
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586594B2

Reaction notes

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