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Methyl iodide → HCID 57270309, compound

HRID 1417553
Notes
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Reaction equation

HRID 1417553 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C(OC([NH:21][C@H:22]1[CH2:47][CH2:46][C@:24]2([O:28][CH2:27][C@H:26]([C:29]3[CH:34]=[C:33]([N:35]4[CH:39]=[CH:38][N:37]=[C:36]4[C:40]([F:43])([F:42])[F:41])[CH:32]=[CH:31][C:30]=3[O:44][CH3:45])[CH2:25]2)[C@@H:23]1[C:48]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=1)=O)C1C=CC=CC=1.IC.[C:57]([O:60][CH2:61][CH3:62])(=[O:59])[CH3:58]>C1COCC1>[CH2:61]([O:60][C:57]([CH2:58][NH:21][C@H:22]1[CH2:47][CH2:46][C@:24]2([O:28][CH2:27][C@H:26]([C:29]3[CH:34]=[C:33]([N:35]4[CH:39]=[CH:38][N:37]=[C:36]4[C:40]([F:42])([F:43])[F:41])[CH:32]=[CH:31][C:30]=3[O:44][CH3:45])[CH2:25]2)[C@@H:23]1[C:48]1[CH:49]=[CH:50][C:51]([F:54])=[CH:52][CH:53]=1)=[O:59])[C:62]1[CH:46]=[CH:47][CH:22]=[CH:23][CH:24]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 67670349HCID 67670349, compound

Product 1

HCID 57270309HCID 57270309, compound

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
0 °C

Procedure

A THF solution of sodium bis(trimethylsily)amide (0.059 mL, 1.0M, 0.059 mmol) was added to an ice-cooled solution of (3S,5R,6R,7S)-7-(benzyloxycarbonylamino)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane (30 mg, 0.049 mmol) in 0.50 mL of dry THF. After stirring for 15 minutes at 0° C., iodomethane (0.0037 mL, 8.4 mg, 0.059 mmol) was added. The mixture was stirred at 0° C., then allowed to warm up to RT for 3 h. The reaction was diluted in 20 mL of ethyl acetate and washed with 10 mL of saturated aqueous sodium bicarbonate, followed by 10 mL of brine. Drying over sodium sulfate and concentration afforded the crude product. Purification by preparative TLC, eluting with 30% ethyl ether in 1:1 toluene/hexane, yielded 7.5 mg of pure title compound and 15 mg of a mixture containing the title compound and recovered starting material. Mass spectrum (NH3/CI): m/z=624.2 (M+1).

Workup

  1. stirringThe mixture was stirred at 0° C.
  2. temperatureto warm up to RT for 3 h
  3. washwashed with 10 mL of saturated aqueous sodium bicarbonate
  4. dry with materialDrying over sodium sulfate and concentration
  5. customafforded the crude product
  6. customPurification by preparative TLC
  7. washeluting with 30% ethyl ether in 1:1 toluene/hexane

Sources & evidence

ORD record
ord-fd1ef373e2cd4d4ba1e33f89a23b3c8d
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05877191

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes