HCID 86659601, compound → HCID 58529808, compound

HRID 1972751Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17](=[N:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:18][CH2:19][CH:20](OC)OC)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC(O)=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([C:17]2[N:25]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

The product from step 2 (20.25 g, 43.68 mmol) was dissolved in 125 mL of AcOH and stirred at 40° C. for 8 h and then concentrated in vacuo. The residue was dissolved in EtOAc (200 mL) and extracted with 50 mL of water, 2×100 mL 2M aq. Na2CO3, brine, dried over Na2SO2. The mixture was filtered through a 1″×4″ pad of SiO2 (pre-wetted with EtOAc) and the pad was washed with 300 mL of EtOAc and the filtrate concentrated in vacuo to give the title compounds as a light, brown syrup that was used without further purification. 1H NMR (300 MHz, DMSO-d6) δ 10.14 (bs, 1H), 7.40-7.24 (m, 5H), 6.59 (d, 1H), 5.90 (dd, 1H), 5.78 (d, 1H), 5.15-4.92 (m, 2H), 4.13 (bd, 1H), 3.99 (bd, 1H), 2.91-2.60 (m, 3H), 1.91 (m, 1H), 1.74-1.62, (m, 1H), 1.42 (s, 12H). ES-MS m/z 400.0 [M+H]+, HPLC RT (min) 3.93

Workup

concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in EtOAc (200 mL)
extractionextracted with 50 mL of water, 2×100 mL 2M aq. Na2CO3, brine
dry with materialdried over Na2SO2
filtrationThe mixture was filtered through a 1″×4″ pad of SiO2 (pre-wetted with EtOAc)
washthe pad was washed with 300 mL of EtOAc
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-b929601f4d934486974b4c7e9f651d99
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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