Sodium Hydroxide → HCID 58293507, compound

HRID 1968249Notes

Reaction equation

[Cl:1][C:2]1[C:11]2[CH2:10][N:9]([C@H:12]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[C:8](=[O:27])[C:7]3=[CH:28][N:29]([S:30]([C:33]4[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=4)(=[O:32])=[O:31])[C:5]([C:6]=23)=[N:4][CH:3]=1.[OH-:40].[Na+]>CO.C1COCC1>[CH2:16]([O:15][C:13](=[O:14])[C@H:12]([NH:9][CH2:10][C:11]1[C:2]([Cl:1])=[CH:3][N:4]=[C:5]2[N:29]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=3)(=[O:32])=[O:31])[CH:28]=[C:7]([C:8]([OH:40])=[O:27])[C:6]=12)[C:23]([CH3:26])([CH3:25])[CH3:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Crude (R)-benzyl 2-(6-chloro-3-oxo-1-tosylpyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3,3-dimethylbutanoate was dissolved in MeOH/THF (50%, 5 mL). Aqueous NaOH (1N, 2 mL) was added. The reaction mixture was stirred at 50° C. for 16 h and was purified via preparative mass trigger LC-MS (AcCN/H2O, 20-50%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow oil (34 mg, 38.9% from Step A starting material). 1H NMR (400 MHz, CD3OD) δ 1.22-1.32 (m, 9 H) 4.92 (br. s., 1 H) 5.18 (d, J=18.95 Hz, 1 H) 5.33 (d, J=18.95 Hz, 1 H) 7.88 (s, 1 H) 8.29 (s, 1 H). [M+H] calc'd for C15H16ClN3O3, 322; found, 322.5.

Workup

customwas purified via preparative mass trigger LC-MS (AcCN/H2O, 20-50%)
customThe fractions were collected
concentrationconcentrated
customdried in vacuo

Sources & evidence

ORD record: ord-8103ca7448cb4e08878fcbe82da15b87
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420816B2

Reaction notes

Loading…