Borane;tetrahydrofuran → HCID 66704634, compound

HRID 424574Notes

Reaction equation

HRID 424574 reaction equation
[CH3:1][N:2]([CH2:10][C:11]([N:13]1[CH2:18][CH2:17][S:16][C:15]2[CH:19]=[CH:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][C:14]1=2)=O)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].B.O1CCCC1>O1CCCC1>[CH3:1][N:2]([CH2:10][CH2:11][N:13]1[CH2:18][CH2:17][S:16][C:15]2[CH:19]=[CH:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][C:14]1=2)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 66704582HCID 66704582, compound

Product 1

HCID 66704634HCID 66704634, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl methyl(2-(6-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)-2-oxoethyl)carbamate (691 mg, 1.881 mmol) in tetrahydrofuran (5 mL) was added borane-tetrahydrofuran complex (1 M in tetrahydrofuran; 5.64 mL, 5.64 mmol). The resulting mixture was then stirred at room temperature for 2 hours and quenched carefully via the slow, dropwise addition of methanol (5 mL). The quenched mixture was then diluted with ethyl acetate and washed sequentially with a 1:1 mixture of water: saturated sodium carbonate (2×) and then with brine. The organic phase was dried, filtered, and concentrated giving a red oil (659 mg, 99%). 1H NMR (DMSO-d6) δ 7.56-7.39 (m, 1H), 7.39-7.31 (m, 1H), 7.24-7.14 (m, 1H), 3.68-3.61 (m, 2H), 3.60-3.49 (m, 2H), 3.48-3.36 (m, 2H), 3.13-3.05 (m, 2H), 2.83 (s, 3H), 1.30, 1.17 (2s, 9H); ESI-MS (m/z, %): 376 (M+Na, 85), 354 (MH+, 24), 298 (100).

Workup

  1. customquenched carefully via the slow,
  2. additiondropwise addition of methanol (5 mL)
  3. additionThe quenched mixture was then diluted with ethyl acetate
  4. washwashed sequentially with a 1:1 mixture of water
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-61ecc8de3eba48e28c9d8a88d286251b
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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