Hydrochloric Acid → HCID 86620426, compound

HRID 1907738Notes

Reaction equation

HRID 1907738 reaction equation
C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].C1COCC1.[C:16]([C:18]1[CH:45]=[CH:44][C:21]([C:22]([NH:24][C:25]2[CH:30]=[C:29]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[CH:28]=[CH:27][C:26]=2[NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:23])=[CH:20][N:19]=1)#[N:17].Cl>>[C:16]([C:18]1[CH:45]=[CH:44][C:21]([C:22]([NH:24][C:25]2[CH:30]=[C:29]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[CH:28]=[CH:27][C:26]=2[NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:23])=[CH:20][N:19]=1)(=[NH:5])[NH2:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 86620427HCID 86620427, compound

Product 1

HCID 86620426HCID 86620426, compoundYield 48%

Procedure

To a 1M solution of lithium bis(trimethylsilyl)amide in THF (0.0.76 mL, 0.76 mmol) at 0° C. was added compound 251 (0.10 g, 0.24 mmol). The reaction mixture was allowed to warm to room temperature, stirred for 18 h, cooled to 0° C., treated with 1N HCl (15 mL), stirred for 30 min and concentrated. The residue was diluted with AcOEt and extracted with H2O. The aqueous phase was collected, neutralized with 1N NaOH, extracted with AcOEt, dried over MgSO4, filtered and concentrated. The resulting brown solid was triturated with diethyl ether to give intermediate 252 (50 mg, 48% yield).

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred for 30 min
  3. concentrationconcentrated
  4. additionThe residue was diluted with AcOEt
  5. extractionextracted with H2O
  6. customThe aqueous phase was collected
  7. extractionextracted with AcOEt
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting brown solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-5eb326ba8ef945759e325ed577b70d0d
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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