Diethyl Ether → HCID 21896696, compound

HRID 719105Notes

Reaction equation

HRID 719105 reaction equation
[O:1]=[S:2]1(=[O:39])[C:8]2[CH:9]=[C:10]([O:14][CH3:15])[C:11](Br)=[CH:12][C:7]=2[N:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][C:4]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[N:3]1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1.[Li][CH2:41]CCC.CI.C(OCC)C>C1COCC1>[O:1]=[S:2]1(=[O:39])[C:8]2[CH:9]=[C:10]([O:14][CH3:15])[C:11]([CH3:41])=[CH:12][C:7]=2[N:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][C:4]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[N:3]1[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 21896663HCID 21896663, compoundHCID 178418339Butyllithium

Product 1

HCID 21896696HCID 21896696, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution (−78° C.) of 1,1-dioxo-2-(4-methoxybenzyl)-3,3dibutyl-5-phenyl-7-bromo-8-methoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (Method 23; 2.10 g, 3.41 mmol) in THF (50 ml) was added dropwise a solution of n-BuLi (2.35 ml, 3.75 mmol, 1.6 M in hexane). After stirring at −78° C. for 20 minutes, MeI (2.42 g, 17.1 mmol) was added. The mixture was stirred at −78° C. for 10 minutes and at room temperature for 18 hours. Diethyl ether (50 ml) was added and the organic phase was washed with 10% NH4Cl (aq, 50 ml) and brine (50 ml). After drying, filtration and concentration the crude product was subjected to flash chromatography (Hexane:EtOAc—95:5) to give 0.4 gram (21%) of the title product as colourless oil. NMR (300 MHz, CDCl3): 0.60–0.70 (m, 6H), 0.70–0.90 (m, 4H), 0.90–1.35 (m, 8H), 2.00 (s, 3H), 3.70 (s, 3H), 3.80 (s, 3H), 4.00–4.20 (m, 2H), 4.35–4.60 (m, 2H), 6.65–6.85 (m, 3H), 6.90–7.10 (m, 3H), 7.15–7.30 (m, 5H).

Workup

  1. stirringThe mixture was stirred at −78° C. for 10 minutes and at room temperature for 18 hours
  2. washthe organic phase was washed with 10% NH4Cl (aq, 50 ml) and brine (50 ml)
  3. customAfter drying
  4. filtrationfiltration and concentration the crude product

Sources & evidence

ORD record
ord-f00ebf1fa8a7437994812d23d9e1fe2f
Source dataset
uspto-grants-2006_11
Patent number
US07132416B2

Reaction notes

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