Methyl iodide → HCID 70268973, compound

HRID 1636374Notes

Reaction equation

HRID 1636374 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[OH:11][CH:12]([C:50]1[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=1)[CH2:13][NH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[N:37]=[C:36]([C@H:38](F)[C:39]4[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=4)[O:35][N:34]=3)=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:19][CH:18]=1.[CH3:56]I.[NH4+].[Cl-]>C1COCC1>[OH:11][CH:12]([C:50]1[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=1)[CH2:13][NH:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[N:37]=[C:36]([C@@H:38]([C:39]4[CH:44]=[CH:43][C:42]([C:45]([F:47])([F:46])[F:48])=[CH:41][CH:40]=4)[CH3:56])[O:35][N:34]=3)=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 21967373HCID 21967373, compound

Product 1

HCID 70268973HCID 70268973, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A 1.0M solution of lithium bis(trimethylsilyl)amide in THF (2.02 mL, 2.02 mmol) was added to a stirred solution of the ester from Example 110, Step A (400 mg, 1.83 mmol) in THF (8 ml) at -78° C. The solution was stirred at -78° C. for 10 min. Methyl iodide (120 μL, 1.93 mmol) was added. The solution was allowed to warm slowly to RT over 12 h. Saturated NH4Cl solution was added and the mixture extracted with diethyl ether (3×). The combined organic phase was washed with water (2×), brine, dried (MgSO4) and the solvent removed in vacuo. Flash chromatography (silica, 2-3% ethyl acetate-hexanes) afforded the title compound (234 mg, 55%) as a colorless liquid: 1H NMR (400 MHz, CDCl3) δ 7.56 (d, J=8.1 Hz, 2H), 7.40 (d, J=8.3 Hz, 2H), 3.77 (q, J=7.1 Hz, 1H), 3.66 (s, 3H), 1.50 (d, J=7.1 Hz, 3H).

Workup

  1. temperatureto warm slowly to RT over 12 h
  2. extractionthe mixture extracted with diethyl ether (3×)
  3. washThe combined organic phase was washed with water (2×), brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5e58f8f2015044fea385c29aec4e2f3e
Source dataset
uspto-grants-2000_03
Patent number
US06034106

Reaction notes

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