Trimethylsilyl triflate → HCID 66832994, compound

HRID 579506Notes

Reaction equation

CC1(C)[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C:5]([CH2:22][CH2:23][CH2:24][CH2:25][B:26]2[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]2)([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:4][O:3]1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>ClCCl>[CH2:10]([O:9][C:7]([NH:6][C:5]([CH2:4][OH:3])([CH2:22][CH2:23][CH2:24][CH2:25][B:26]1[O:30][C:29]([CH3:31])([CH3:32])[C:28]([CH3:34])([CH3:33])[O:27]1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

While under an argon atmosphere, a solution of 3-benzyl 4-ethyl 2,2-dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)oxazolidine-3,4-dicarboxylate (350 mg, 0.72 mmol) in dichloromethane (5 mL) was cooled to −40° C. and carefully treated with trimethylsilyltrifluoromethane sulfonate (1.09 g, 4.29 mmol, 0.94 mL). After stirring for 30 minutes the solution was warmed to 0° C. and stirred an additional 2 h, concentrated and purified using a combiflash system (12 g silica gel column, eluting with 20-100% ethyl acetate in heptanes) to give ethyl 2-(benzyloxycarbonylamino)-2-(hydroxymethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate (180 mg, 56%). 1HNMR (CDCl3) δ 7.38-7.31 (m, 5H), 5.81 (bs, 1H), 5.10 (s, 2H), 4.25-4.23 (m, 3H), 3.84 (d, 1H), 2.84 (m, 1H), 1.76-1.68 (m, 1H), 1.41-1.35 (m, 2H), 1.28 (t, 3H), 1.23 (s, 12H), 1.11-1.03 (m, 1H), 1.29 (m, 4H), 0.75 (t, 2H). MS found for C23H36BNO7 m/z[450 (M+1)].

Workup

stirringstirred an additional 2 h
concentrationconcentrated
custompurified
washa combiflash system (12 g silica gel column, eluting with 20-100% ethyl acetate in heptanes)

Sources & evidence

ORD record: ord-55e814fa1f2e49f290d8a3527f676194
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040703B2

Reaction notes

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