Ammonium Chloride → HCID 90370280, compound

HRID 2176025Notes

Reaction equation

HRID 2176025 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][C:12]([CH3:48])([CH2:17][CH2:18][C:19](=[O:47])[N:20]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]2[O:34][C:35](=[O:46])[C:36]3[C:41]4[CH2:42][CH2:43][CH2:44][CH2:45][C:40]=4[S:39][C:37]=3[N:38]=2)[CH:28]=1)[CH:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:13]([O:15][CH3:16])=[O:14].[N:49]1([CH2:55][CH2:56][C:57]2[CH:63]=[CH:62][C:60]([NH2:61])=[CH:59][CH:58]=2)[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1.[Cl-].[NH4+]>C1COCC1>[CH3:48][C:12]([CH3:11])([CH2:17][CH2:18][C:19]([N:20]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33](=[O:34])[NH:38][C:37]2[S:39][C:40]3[CH2:45][CH2:44][CH2:43][CH2:42][C:41]=3[C:36]=2[C:35](=[O:46])[NH:61][C:60]2[CH:62]=[CH:63][C:57]([CH2:56][CH2:55][N:49]3[CH2:50][CH2:51][O:52][CH2:53][CH2:54]3)=[CH:58][CH:59]=2)[CH:28]=1)[CH:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[O:47])[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 219550254-(2-Morpholinoethyl)anilineHCID 90370335HCID 90370335, compound

Product 1

HCID 90370280HCID 90370280, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hexamethyldisilazide (1.0 M in THF) 1.1 mL was added dropwise to a mixture of 200 mg of methyl 2,2-dimethyl-5-oxo-5-{[3-(4-oxo-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-2-yl)benzyl](pentan-3-yl)amino}pentanoate, 90 mg of 4-[2-(morpholin-4-yl)ethyl]aniline, and 5.0 mL of THF under ice cooling, followed by stirring for 30 minutes at the same temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), thereby obtaining 164 mg of methyl 2,2-dimethyl-5-[(3-{[3-({4-[2-(morpholin-4-yl)ethyl]phenyl}carbamoyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]carbamoyl}benzyl)(pentan-3-yl)amino]-5-oxopentanoate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-9cc6f6daec1b4aebb2687e281444326b
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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