HCID 86693880, compound → HCID 71715676, compound

HRID 1842836Notes

Reaction equation

[Si]([O:8][CH2:9][C@H:10]1[C:19]2([CH2:21][CH2:20]2)[C@@H:18]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[NH:24][C:23]2=[O:29])[C@@H:12]2[O:13]C(C)(C)[O:15][C@H:11]12)(C(C)(C)C)(C)C>C(O)(C(F)(F)F)=O.O>[OH:13][C@@H:12]1[C@H:11]([OH:15])[C@@H:10]([CH2:9][OH:8])[C:19]2([CH2:21][CH2:20]2)[C@H:18]1[N:22]1[CH:27]=[CH:26][C:25](=[O:28])[NH:24][C:23]1=[O:29]

Participants

Conditions

Temperature: 50 °C

Procedure

Compound 16 (0.2 g, 0.47 mmol) was dissolved in 20 mL of CF3COOH/H2O (2:1, v/v) and heated to 50° C. for 3 hr. The solvent was removed under vacuum and the residue was co-evaporated with ethanol (10 mL×3) under vacuum. The residue was purified by column chromatography on a silica gel (7% MeOH/CH2Cl2) to give 17 (100 mg, 79%) as white foam. mp 114-116° C.; [α]24D 9.84° (c 0.26, MeOH); UV (MeOH) λmax 265 nm (ε11713, pH 2), 265 nm (ε11887, pH 7), 264 nm (ε9153, pH 11); 1H NMR (500 MHz, CD3OD-d6) δ 7.50 (d, J=8.5 Hz, 1H), 5.68 (d, J=8.5 Hz, 1 H), 4.77-4.73 (m, 2 H), 4.62 (d, J=3 Hz, 1 H), 3.71 (dd, J=4.5 & 11.0 Hz, 1 H), 3.62 (dd, J=5 & 11.0 Hz, 1 H), 2.26 (m, 1 H), 0.87 (m, 2H), 0.81 (m, 1H), 0.33 (m, 1H) ; 13C NMR (125 MHz, CD3OD) δ 165.1, 152.2, 146.3, 109.9, 74.3, 72.4, 63.4, 51.1,29.8, 28.7, 10.9; HR-MS Calcd. For (C12H16N2O5+H)+ 269.1059, found 269.1261.

Workup

customThe solvent was removed under vacuum
customThe residue was purified by column chromatography on a silica gel (7% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-ad5c9b459c1b4ff1acb66384cb58a757
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946242B2

Reaction notes

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