HCID 22874560, compound → HCID 22874559, compound

HRID 263842Notes

Reaction equation

[S:1]([NH:17][C@@H:18]([CH2:23][NH:24]C(OC(C)(C)C)=O)[C:19]([O:21][CH3:22])=[O:20])([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2]>CCOC(C)=O>[S:1]([NH:17][C@@H:18]([CH2:23][NH2:24])[C:19]([O:21][CH3:22])=[O:20])([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:2])=[O:3]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2-4 (0.43 g, 0.95 mmol) was suspended in EtOAc (15 mL) and cooled to -78° C. HCl gas was bubbled through the solution and the solution became homogenous. The solution was placed in an ice bath for 0.5 h, then concentrated to give 2-5 as an amorphous yellow solid. 1H NMR (300 MHz, CD3OD) δ8.97 (d, 1H), 8.62 (d, 1H), 8.44 (d, 1H), 8.18 (d, 1H), 7.95 (t, 2H), 4.25 (dd, 1H), 3.52 (s, 6H), 3.35 (dd, 1H), 3.12 (dd, 1H), 3.06 (s, 3H).

Workup

customHCl gas was bubbled through the solution
concentrationconcentrated

Sources & evidence

ORD record: ord-4973d715b5ea41af80efbf0dd2f1ddec
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05646000

Reaction notes

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