Iodoethane → HCID 68558057, compound

HRID 20418Notes

Reaction equation

HRID 20418 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:11]([O:15][C:16]([N:18]1[C@@H:23]([C@@H:24]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@@H:25]([N:35]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:26][C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=2)[CH2:22][O:21][C:20](=[O:58])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].I[CH2:60][CH3:61]>O1CCCC1>[C:11]([O:15][C:16]([N:18]1[C@@H:23]([C@@H:24]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@@H:25]([N:35]([CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:26][C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=2)[CH2:22][O:21][C:20](=[O:58])[C@@H:19]1[CH2:60][CH3:61])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2733832Lithium HexamethyldisilazideHCID 68560976HCID 68560976, compound

Product 1

HCID 68558057HCID 68558057, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Slowly add lithium hexamethyldisilazide (2.28 mL, 2.28 mmol, 1.0 M in tetrahydrofuran) at −78° C. under nitrogen to a solution of (R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-oxomorpholine-4-carboxylic acid tert-butyl ester) (1 g, 1.52 mmol) and iodoethane (1.24 mL, 15.2 mmol) in anhydrous tetrahydrofuran (10 mL). Stir at −78° C. for 45 minutes, remove the bath and stir for 1.5 hours. Add water and ethyl acetate. Separate the organic layer and extract the aqueous layer with ethyl acetate. Combine the organic layers, dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 90:10 hexane:ethyl acetate) to give the desired compound as a white solid (848 mg, 82%).

Workup

  1. customat −78° C.
  2. customremove the bath
  3. stirringstir for 1.5 hours
  4. customSeparate the organic layer
  5. extractionextract the aqueous layer with ethyl acetate
  6. dry with materialdry (sodium sulfate)
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify
  10. wash(silica gel chromatography, eluting with 90:10 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-77e767511eab4050ad4d4bd2e3374ef3
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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