Iodine → HCID 58786611, compound

HRID 1376067Notes

Reaction equation

HRID 1376067 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:15][NH:16][C:17](=O)[CH:18]([CH3:20])[CH3:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O1CCCC1.CCN(C(C)C)C(C)C.II>C1COCC1.CCOC(C)=O.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:15][NH:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 4

HCID 807IodineHCID 81531DiisopropylethylamineHCID 2723981Borane;tetrahydrofuranHCID 58786757HCID 58786757, compound

Product 1

HCID 58786611HCID 58786611, compoundYield 76.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product from Step I (1.23 g, 3.21 mmol) and borane-tetrahydrofurane complex (9.6 mL, 9.63 mmol, 1 M in THF) in THF (20 mL) was heated at 60° C. for 1 hour. The mixture was allowed to cool to ambient temperature followed by addition of MeOH (5 mL) and DIPEA (7.5 mL). Next, iodine (1.62 g, 6.42 mmol) in THF (10 mL) was added and the mixture stirred for 30 min. The mixture was diluted with EtOAc and successively washed with 10% aqueous Na2S2O5 and brine, dried (Na2SO4), and evaporated. The residue was purified by flash chromatography (hexane:EtOAc 1:1→EtOAc→EtOAc:MeOH:NEt3 90:5:5) to afford the title compound (904 mg) as a yellow oil. MS m/z 368.3 (M++1).

Workup

  1. washsuccessively washed with 10% aqueous Na2S2O5 and brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by flash chromatography (hexane:EtOAc 1:1→EtOAc→EtOAc:MeOH:NEt3 90:5:5)

Sources & evidence

ORD record
ord-27c919612baf4f04a361997e23b7f185
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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