Hydrochloric Acid → HCID 178493589, compound

HRID 39664Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:27]=[CH:26][C:8]2[N:9]=[C:10]([C:12]3[N:13]([CH3:25])[CH:14]=[C:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:16]=3)[NH:11][C:7]=2[C:6]=1[O:28][CH3:29])=[O:4].Cl>[OH-].[Na+]>[C:21]([O:20][C:18]([NH:17][C:15]1[CH:16]=[C:12]([C:10]2[NH:11][C:7]3[C:6]([O:28][CH3:29])=[C:5]([C:3]([OH:4])=[O:2])[CH:27]=[CH:26][C:8]=3[N:9]=2)[N:13]([CH3:25])[CH:14]=1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl ester 16 (51 mg, 0.13 mmol) was dissolved in 1 M NaOH (1:1 dioxane/H2O, 5 mL) and stirred overnight at r.t and an additional 3 h at 50° C. The reaction mixture was cooled to 0° C. and 1N HCl was added dropwise to adjust the pH to 3-4, while a white precipitate was formed. Separation of the product was accomplished by centrifugation and decanting of the supernatant. Lyophilization gave 36 mg (73%) of 17 as a beige solid. Data of 17: 1H NMR (500 MHz, DMSO-d6): δ 1.40 (s, 9H), 3.97 (s, 3H), 4.28 (s, 3H), 6.76 (s, 1H), 6.92 (s, 1H), 7.02 (d, J=8.2 Hz, 1H), 7.44 (d, J=8.2 Hz, 1H), 9.13 (s, 1H), 12.20 (brs, 1H). 13C NMR (125 MHz, DMSO-d6): δ 27.80, 36.34, 60.78, 78.29, 102.88, 104.47, 114.67, 116.12, 119.79, 123.54, 124.96, 135.00, 139.02, 145.90, 150.62, 152.78, 167.70. UV (H2O): λmax 319. MS (ESI): m/z (rel intensity) 387 (100). HRMS (FAB): calcd for C19H23N4O5, 387.1668; found, 387.1658.

Workup

temperatureThe reaction mixture was cooled to 0° C.
customwhile a white precipitate was formed
customSeparation of the product
customdecanting of the supernatant

Sources & evidence

ORD record: ord-be53603c83a64328b94e5b2419c5f6ca
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524899B2

Reaction notes

Loading…