Hydrochloric Acid → HCID 58764280, compound

HRID 1438251Notes

Reaction equation

[CH:1]1([C:6]2([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C@H:34]([NH:36]C(=O)OC(C)(C)C)[CH3:35])=[CH:30][CH:29]=3)[CH2:11][C:10]([OH:12])=[C:9]([CH2:13][C:14]3[N:24]=[C:17]4[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)[C:8](=[O:25])[O:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[NH2:36][C@@H:34]([C:31]1[CH:30]=[CH:29][C:28]([CH2:27][CH2:26][C:6]2([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[O:7][C:8](=[O:25])[C:9]([CH2:13][C:14]3[N:24]=[C:17]4[N:18]=[C:19]([CH3:23])[CH:20]=[C:21]([CH3:22])[N:16]4[N:15]=3)=[C:10]([OH:12])[CH2:11]2)=[CH:33][CH:32]=1)[CH3:35]

Participants

Conditions

Temperature: 25 °C

Procedure

To a stirred solution of tert-butyl (1R)-1-[4-(2-{2-cyclopentyl-5-[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl]-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl}ethyl)phenyl]ethylcarbamate (0.58 g, 0.98 mmol, example A(91)) in dioxane (2 mL) under argon was added 4 N HCl in dioxane (2 mL). The resulting solution was stirred at 25° C. for 30 minutes. The solvents were completely evaporated and the resultant white solid was recrystalized from ethyl acetate to give the product (0.40 g, 80%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 1.56-1.77 (m, 11H), 2.14-2.18 (m, 2H), 2.57-2.86 (m, 10H), 3.77-3.94 (m, 2H), 4.40-4.43 (m, 1H), 6.6 (brs, 2H), 7.21 (s, 1H), 7.38 (d, J=7.9 Hz, 2H), 7.48 (d, J=7.9 Hz, 2H), 8.56 (s, 1H), 11.2 (s, 1H). Anal. Calcd. For C28H35N5O3. 1.0HCl. 1.0H2O: C, 63.74; H, 7.26; N, 13.27. Found: C, 63.60; H, 7.48; N, 13.20. ESIMS (MH+): 527.

Workup

customThe solvents were completely evaporated
customthe resultant white solid was recrystalized from ethyl acetate

Sources & evidence

ORD record: ord-7a9eeb0ace294cd9bdd8a2032b186632
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622605B2

Reaction notes

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