Ammonia → HCID 21356619, compound

HRID 1167428Notes

Reaction equation

HRID 1167428 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([O:6][CH2:7][C@@H:8]2[O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH2:25][CH2:24][N:23]([CH:26]5[CH2:31][O:30]C(C)(C)[O:28][CH2:27]5)[CH2:22][CH:21]=4)=[C:16]([F:34])[CH:15]=3)[CH2:9]2)=[N:2]1.Cl.N>C1COCC1>[O:1]1[CH:5]=[CH:4][C:3]([O:6][CH2:7][C@@H:8]2[O:12][C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH2:25][CH2:24][N:23]([CH:26]([CH2:27][OH:28])[CH2:31][OH:30])[CH2:22][CH:21]=4)=[C:16]([F:34])[CH:15]=3)[CH2:9]2)=[N:2]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 21356620HCID 21356620, compound

Product 1

HCID 21356619HCID 21356619, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Example 59 (203 mg, 0.43 mmol) in THF (15 ml) was added 1N HCl (10 ml). The reaction was allowed to stir at ambient temperature for 18 hours. The reaction was basified with ammonia solution until aqueous layer was pH12. The reaction was extracted with EtOAc and the combined organic phases were washed with sat NaCl and then dried over MgSO4 and evaporated under reduced pressure. The resulting yellow oil was triturated with ether to give the title compound as a pale yellow solid (167 mg, 90%). MS: ESP+ (M+H)+=434.

Workup

  1. extractionThe reaction was extracted with EtOAc
  2. washthe combined organic phases were washed with sat NaCl
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe resulting yellow oil was triturated with ether

Sources & evidence

ORD record
ord-0ab64e3f83d24145ae26521b8858d488
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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