Borane;tetrahydrofuran → HCID 66704717, compound

HRID 1917210Notes

Reaction equation

HRID 1917210 reaction equation
[CH2:1]([N:3]([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:15]1=2)=O)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].B.O1CCCC1>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:3]([CH2:11][CH2:12][N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[CH:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][C:15]1=2)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:7])[CH3:8])[CH3:2]

Participants

5

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 66704567HCID 66704567, compound

Product 1

HCID 66704717HCID 66704717, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl ethyl(2-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)-2-oxoethyl)carbamate (1.01 g, 2.65 mmol) in tetrahydrofuran (5 mL) was added borane-tetrahydrofuran complex (1 M in tetrahydrofuran; 7.94 mL, 7.94 mmol). The resulting mixture was stirred at room temperature for 2 hours. The mixture was then quenched via the slow dropwise addition (to avoid excessive bubbling) of MeOH (5 mL). The quenched reaction was then diluted with ethyl acetate and washed with water (2×) and saturated sodium carbonate (2×). The organic phase was dried, filtered, and concentrated, giving a red-orange oil (925 mg, 95%). 1H NMR (DMSO-d6) δ 7.59-7.41 (m, 1H), 7.39-7.32 (m, 1H), 7.24-7.13 (m, 1H), 3.69-3.62 (m, 2H), 3.58-3.48 (m, 2H), 3.45-3.35 (m, 2H), 3.28-3.16 (m, 2H), 3.15-3.08 (m, 2H), 1.32, 1.24 (2s, 9H), 1.04 (t, J=6.9 Hz, 3H); ESI-MS (m/z, %): 390 (M+Na, 70), 368 (MH+, 12), 312 (47), 268 (100).

Workup

  1. customThe mixture was then quenched via the slow dropwise addition (to avoid excessive bubbling) of MeOH (5 mL)
  2. customThe quenched reaction
  3. washwashed with water (2×) and saturated sodium carbonate (2×)
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e426846c605c494eb859717907f27358
Source dataset
uspto-grants-2013_12
Patent number
US08618286B2

Reaction notes

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