N,N-Diethylethanamine trihydrofluoride → HCID 86628924, compound

HRID 1919455Notes

Reaction equation

F.F.F.C(N(CC)CC)C.[C:11]([NH:14][CH2:15][CH2:16][CH2:17][S:18]([O:21][CH2:22][C:23]([CH3:45])([CH3:44])[C@@H:24]([O:36][Si](C)(C)C(C)(C)C)[C:25]([O:27][CH2:28][C:29]1[O:30][C:31](=[O:35])[O:32][C:33]=1[CH3:34])=[O:26])(=[O:20])=[O:19])(=[O:13])[CH3:12]>O1CCCC1>[C:11]([NH:14][CH2:15][CH2:16][CH2:17][S:18]([O:21][CH2:22][C:23]([CH3:45])([CH3:44])[C@@H:24]([OH:36])[C:25]([O:27][CH2:28][C:29]1[O:30][C:31](=[O:35])[O:32][C:33]=1[CH3:34])=[O:26])(=[O:19])=[O:20])(=[O:13])[CH3:12]

Participants

Conditions

Temperature: 55 °C

Procedure

Following the general procedure for the cleavage of silyl ethers with triethylamine trihydrofluoride of Description 20, a mixture of (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl (2R)-4-{[(3-acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(1,1,2,22-tetramethyl-1-silapropoxy)butanoate (48a) (100 mg, 0.18 mmol) and triethylamine trihydrofluoride (Et3N.3HF) 150 μL (149 mg, 0.93 mmol) in 2 mL of tetrahydrofuran (THF) was stirred overnight at ca. 50-60° C. (oil bath). After work-up and further purification by mass-guided preparative HPLC and lyophilization of the solvents, 6.2 mg (8.1% yield) of the title compound (48) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=1.03 (s, 3H), 1.11 (s, 3H), 2.01 (s, 3H), 2.04-2.11 (m, 2H), 2.22 (s, 3H), 3.10-3.23 (m, 2H), 3.31-3.46 (m, 2H), 4.00 (d, J=9.2 Hz, 1H), 4.07-4.10 (m, 2H), 4.93 (d, J=14.0 Hz, 1H), 5.03 (d, J=13.6 Hz, 1H), 5.86-5.88 (br. m, 1H) ppm. MS (ESI) m/z 424.01 (M+H)+, 446.01 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

customAfter work-up and further purification by mass-guided preparative HPLC and lyophilization of the solvents

Sources & evidence

ORD record: ord-16e21cc6d8f94188a02d6db6b795fe31
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168617B2

Reaction notes

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