2-(2-Boc-aminoethoxy)ethanol → HCID 69310743, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8]CCOCCO)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[CH:16]([C:23]1[CH:27]=[C:26]([CH2:28][CH2:29][CH2:30][O:31][C:32]2[C:37]([CH3:38])=[CH:36][C:35]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:34][C:33]=2[CH3:45])[O:25][N:24]=1)[CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22]>>[C:1]([O:5][C:6]([NH:8][CH:16]([C:23]1[CH:27]=[C:26]([CH2:28][CH2:29][CH2:30][O:31][C:32]2[C:37]([CH3:38])=[CH:36][C:35]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:34][C:33]=2[CH3:45])[O:25][N:24]=1)[CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
Reaction of the bromomethyl compound of example 5 with 5-t-butyloxycarbonylamino-3-oxapentanol using essentially the same method as described in example 5 for Compound 7 gave the adduct, 3-(1-t-butyloxycarbonylamino-3,6-dioxaheptyl)-5-[3-[2,6-dimethyl-4-phenylphenoxy]-propyl]-isoxazole in 91% yield. Trifluoroacetic acid (1 ml) was added to a solution of the adduct (240 mg, 0.46 mmol) in DCM (10 ml) and the reaction was allowed to stir under argon for 2 hours. The reaction was concentrated at vacuum then the crude product was partitioned between brine/sodium bicarbonate (1:1, 20 ml) and ethyl acetate (2×100 ml). The combined organic phase was dried (Na2SO4) and concentrated, the crude product was chromatographed on silica gel (20 g); eluent 92.5:7.5 DCM/(10% ammonia in methanol) to give 3-(1-amino-3,6-dioxaheptyl)-5-[3-[2,6-dimethyl-4-phenylphenoxy]-propyl]-isoxazole (Compound 14) in 71% yield. 1 H nmr (CD3OD): δ=7.5-7.15 (m, 7H); 6.24 (s, 1H); 4.55 (s, 2H); 3.81 (t, 2H); 3.61 (s, 4H); 3.46 (t, 2H); 3.03 (t, 2H); 2.72 (t, 2H); 2.26 (s, 6H) and 2.16 (m, 2H). MS (ES): (M+H)+ 425.2428 (Calc. C25H32N2O4H=425.2432).
Sources & evidence
- ORD record
- ord-053efb1b618c483388d049837f652ff6
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371755B1
Reaction notes
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