Triethylamine → HCID 10173067, compound
Reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28][Si](C(C)(C)C)(C)C)[C@@H:14]([O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@@:12]3([CH3:36])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.C(N(CC)CC)C.F.F.F.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:14]([O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C@@:12]3([CH3:36])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1Participants
6
Procedure
To a solution of the compound from Step J (230 mg, 0.44 mmol) in anhydrous THF (5 mL), was added triethylamine (300 μL, 2.14 mmol) and triethylamine trihydrofluoride (750 μL, 4.5 mmol). The solution was stirred overnight at room temperature. The reaction mixture was then diluted with ethyl acetate (30 mL) and washed with saturated aqueous sodium bicarbonate (3×10 mL) and water (10 mL). After drying the organic layer over anhydrous sodium sulfate and filtration, the solvent was evaporated. The resulting oil was purified on a silica gel column eluting with 1:1 acetone/CH2Cl2 followed by 10% MeOH in CH2Cl2. The appropriate fractions were concentrated and lyophilized to afford the title compound as a colorless powder (90 mg).
Workup
- washwashed with saturated aqueous sodium bicarbonate (3×10 mL) and water (10 mL)
- customAfter drying the organic layer
- filtrationover anhydrous sodium sulfate and filtration
- customthe solvent was evaporated
- customThe resulting oil was purified on a silica gel column
- washeluting with 1:1 acetone/CH2Cl2
- concentrationThe appropriate fractions were concentrated
Sources & evidence
- ORD record
- ord-be38c2c4707a40dda26195b0571af317
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07323453B2
Reaction notes
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