Sodium Iodide → HCID 59000781, compound

HRID 1594016Notes

Reaction equation

HRID 1594016 reaction equation
CS(OS(C)(=O)=O)(=O)=O.CCN(CC)CC.[CH2:17]([O:19][C:20]([C:22]1[C:23]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[C:24]([CH2:43][CH2:44][CH2:45]O)[N:25]2[C:30]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[CH:28][C:27]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[N:26]2)=[O:21])[CH3:18].[Na+].[I-].[P:54]([O:61]CC)([O:58][CH2:59][CH3:60])[O:55][CH2:56][CH3:57]>C(Cl)Cl>[CH2:17]([O:19][C:20]([C:22]1[C:23]([C:47]([O:49][CH2:50][CH3:51])=[O:48])=[C:24]([CH2:43][CH2:44][CH2:45][P:54]([O:58][CH2:59][CH3:60])([O:55][CH2:56][CH3:57])=[O:61])[N:25]2[C:30]=1[C:29]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[CH:28][C:27]([N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[N:26]2)=[O:21])[CH3:18]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 31215Triethyl phosphiteHCID 81560Methanesulfonic anhydrideHCID 52943384HCID 52943384, compound

Product 1

HCID 59000781HCID 59000781, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methanesulfonic anhydride (136 mg, 0.78 mmol) and NEt3 (145 μL, 1.04 mmol) were added to a solution of 41 (125 mg, 0.26 mmol) in CH2Cl2 (15 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at 0° C. for 30 min. and at ambient temperature for 8 h. The reaction mixture was diluted with CH2Cl2 (20 mL) and washed with saturated aqueous NaHCO3, brine, dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil. A mixture of the oil (68.5 mg, 0.122 mmol) and NaI (183 mg, 1.22 mmol) in P(OEt)3 (5 mL) was heated at 120° C. for 24 h. The P(OEt)3 was removed in vacuo and the residue was purified by flash chromatography (silica gel, 0-4% MeOH/CH2Cl2) to provide the title compound. 1H NMR (DMSO-d6) δ 0.89 (t, J=7.2 Hz, 3H), 1.20 (m, 9H), 1.85 (m, 2H), 3.24 (m, 2H), 3.52 (m, 6H), 3.71 (m, 4H), 3.94 (m, 6H), 4.17 (q, J=7.1 Hz, 2H), 6.79 (s, 1H), 7.40 (m, 2H), 7.46 (m, 3H). Mass Spectrum (ESI+) m/e=602.2 (M+H).

Workup

  1. washwashed with saturated aqueous NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a yellow oil
  6. temperaturewas heated at 120° C. for 24 h
  7. customThe P(OEt)3 was removed in vacuo
  8. customthe residue was purified by flash chromatography (silica gel, 0-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-bb52dc45c975453494591c2142cb403b
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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