Borane;tetrahydrofuran → HCID 59144132, compound

HRID 424599Notes

Reaction equation

HRID 424599 reaction equation
[CH2:1]([N:3]([CH2:11][C:12]([N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:15]1=2)=O)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].B.C1COCC1>O1CCCC1>[CH2:1]([N:3]([CH2:11][CH2:12][N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:15]1=2)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:7])[CH3:8])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 59144102HCID 59144102, compound

Product 1

HCID 59144132HCID 59144132, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl ethyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)-2-oxoethyl)carbamate (0.8 g, 2.097 mmol) in anhydrous tetrahydrofuran (5 mL) was treated with borane-THF complex (1M in THF; 6.29 mL, 6.29 mmol) and stirred at room temperature for 3 hours. The reaction was quenched dropwise with methanol (10 mL) and then concentrated. The crude residue was diluted with methanol (25 mL) and refluxed for 10 minutes. The mixture was then concentrated, and the residue was subjected to column chromatography on silica gel (1:9-3:7 EtOAc:CH2Cl2) to give a yellow syrup (0.493 g, 64%). 1H-NMR (DMSO-d6) δ 7.85-7.78 (m, 2H), 6.94-6.85 (m, 1H), 3.76-3.79 (m, 2H), 3.62-3.57 (m, 2H), 3.37-3.33 (m, 2H), 3.22-3.19 (m, 2H), 3.08-3.04 (m, 2H), 1.35 and 1.30 (2×brs, 9H), 1.03 (t, J=6.9 Hz, 3H). ESI-MS (m/z, %): 390 (M+Na, 67%), 368 (MH+, 17%), 312 (83%), 268 (100%).

Workup

  1. customThe reaction was quenched dropwise with methanol (10 mL)
  2. concentrationconcentrated
  3. additionThe crude residue was diluted with methanol (25 mL)
  4. temperaturerefluxed for 10 minutes
  5. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-8d332adb1289479096fcd50fb627818b
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

Loading…