Sodium Iodide → HCID 90037702, compound

HRID 1055447Notes

Reaction equation

HRID 1055447 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([O:15][C:16](=[O:30])[NH:17][C@@H:18]1[C:24](=[O:25])[NH:23][C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[O:20][CH2:19]1)([CH3:14])([CH3:13])[CH3:12].Cl[CH2:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[CH3:43].[Na+].[I-]>C1COCC1>[CH3:43][C:34]1[CH:35]=[CH:36][C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:33]=1[CH2:32][N:23]1[C:24](=[O:25])[C@@H:18]([NH:17][C:16](=[O:30])[O:15][C:11]([CH3:14])([CH3:12])[CH3:13])[CH2:19][O:20][C:21]2[CH:29]=[CH:28][CH:27]=[CH:26][C:22]1=2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 811061-Chloromethyl-2-methylnaphthaleneHCID 2733832Lithium HexamethyldisilazideHCID 18599719(S)-tert-Butyl (4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-yl)carbamate

Product 1

HCID 90037702HCID 90037702, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 M lithium bis(trimethylsilyl) amide in THF (3.07 mL, 1 eq) was added to a solution of ((S)-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-carbamic acid-t-butyl ester (855 mg, 3.07 mmol, 1.0 eq) in THF (10 mL) at −78° C. After 30 min. 1-(chloromethyl)-2-methylnaphthalene (586 mg, 3.07 mmol, 1 eq) and NaI (461 mg, 3.07 mmol, 1 eq) were added and the mixture warmed to RT over 2 h. The solvent was removed and the residue was suspened in EtOAc and washed with H2O. The aqueous extracts were extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by silica chromatography to afford (S)-tert-butyl 5-((2-methylnaphthalen-1-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylcarbamate (1.01 g, 75%) as a yellow foam.

Workup

  1. customThe solvent was removed
  2. washwashed with H2O
  3. extractionThe aqueous extracts were extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-addf5d989b6548ac96576890a8d0ea31
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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