Iodoethane → HCID 67509654, compound

HRID 1770718Notes

Reaction equation

HRID 1770718 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][S:12]([CH2:15][CH2:16][C:17]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:19])[CH3:18])(=[O:14])=[O:13].[CH2:31](I)[CH3:32]>CN(C=O)C.CCOC(C)=O>[CH2:31]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][S:12]([CH2:15][CH2:16][C:17]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([CH3:18])[CH3:19])(=[O:13])=[O:14])[CH3:32]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 67509059HCID 67509059, compound

Product 1

HCID 67509654HCID 67509654, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 60% sodium hydride (50 mg, 1.3 mmol) in DMF (4 ml) was cooled to 0° C. under N2 and benzyl 4-(2-(2-(2-hydroxyethoxy)ethoxy)ethylsulfonyl)-2-methylbutan-2-ylcarbamate (419.6 mg, 1.005 mmol) in DMF (1 ml) was added dropwise. Ethyl iodide (100 ul, 1.25 mmol) was added dropwise. The solution was stirred for 3 h, diluted with EtOAc (300 ml), washed with 2×100 ml sat. NaCl, dried on MgSO4, and concentrated in vacuo. The resulting residue was purified by flash chromatography (30% to 80% EtOAc in hexanes) to afford the title compound as a clear oil (119.8 mg, 0.2691 mmol, 27%). 1H NMR (CDCl3, 400 MHz) δ 1.18 (t, J=4.4 Hz, 3H), 1.32 (s, 6H), 2.17-2.21 (m, 2H), 3.12-3.17 (m, 2H), 3.48-3.58 (m, 10H), 3.87 (dd, J=5.6, 5.6 Hz, 2H), 5.03-5.06 (m, 3H), 7.3-7.4 (m, 5H). LRMS (ESI/APCI): 446 [M+H]+, 468 [M+Na]+.

Workup

  1. washwashed with 2×100 ml sat. NaCl
  2. customdried on MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by flash chromatography (30% to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d414c8dbf48d464092f05f2bac9b445d
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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