Dimethylformamide → HCID 57971674, compound
Reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]([OH:13])=O)[S:8][C:7]=2[CH:14]=1.C1CN([P+](Br)(N2[CH2:30][CH2:29][CH2:28]C2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(O[CH2:44][CH2:45][O:46][NH2:47])C(C)C.CCN(C(C)C)C(C)C.CN([CH:60]=[O:61])C>O.CCOC(C)=O>[CH2:60]([O:61][CH:45]([O:46][NH:47][C:11]([C:9]1[S:8][C:7]2[CH:14]=[C:3]([CH2:2][OH:1])[CH:4]=[CH:5][C:6]=2[CH:10]=1)=[O:13])[CH3:44])[CH:29]([CH3:28])[CH3:30]Participants
Procedure
To a solution of 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid (1.76 g, 8.4 mmol, 1 eq) in DMF was added PyBrOP (4.3 g, 9.2 mmol), O-(isobutoxy-ethyl)-hydroxylamine (11.5 mL, 84.0 mmol) (prepared via procedure in wool 60785) and DIPEA (2.9 mL, 16.7 mmol). The reaction mixture was allowed to stir at r.t. for 2 h then diluted with water (40 mL) and EtOAc (40 mL). The organic layer was isolated, washed with brine (50 mL) and concentrated. The residue was purified by chromatography on silica gel eluting with EtOAc/heptane (1:1) to afford the title compound (1.8 g, 67% over 2 steps). LCMS m/z 322 [M+−H]+, 1H NMR (300 MHz, MeOD), δ: 0.83 (6H, d J=6.6 Hz, 2×CH3), 1.32 (3H, d J=5.9 Hz, CH3), 1.75 (1H, m, CH), 3.38 (2H, m, CH2), 4.63 (2H, s, CH2), 4.95 (1H, m, CH), 7.32 (1H, d J=8.2 Hz, ArH), 7.77 (3H, m, ArH).
Workup
- customThe organic layer was isolated
- washwashed with brine (50 mL)
- concentrationconcentrated
- customThe residue was purified by chromatography on silica gel eluting with EtOAc/heptane (1:1)
Sources & evidence
- ORD record
- ord-3ff27074e38e49afa0606653410bf0db
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133104B2
Reaction notes
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