Diisopropylethylamine → HCID 89930808, compound

HRID 527757Notes

Reaction equation

HRID 527757 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]([OH:15])=O)[CH2:11][Si:10]([CH3:17])([CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[F:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C@H:44]([NH:46][CH2:47][C:48]1[CH:57]=[CH:56][C:51]([C:52]([O:54][CH3:55])=[O:53])=[CH:50][CH:49]=1)[CH3:45].CCN(C(C)C)C(C)C>C(Cl)Cl.[Cl-].[Na+].O>[F:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C@H:44]([N:46]([CH2:47][C:48]1[CH:49]=[CH:50][C:51]([C:52]([O:54][CH3:55])=[O:53])=[CH:56][CH:57]=1)[C:13]([C@H:12]1[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][Si:10]([CH3:17])([CH3:16])[CH2:11]1)=[O:15])[CH3:45]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 10825193(R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 81364514HCID 81364514, compound

Product 1

HCID 89930808HCID 89930808, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (R)-1-(tert-butoxycarbonyl)-3,3-dimethyl-1,3-azasilolidine-5-carboxylic acid (0.25 g, 0.96 mmol) in DCM (5 mL) were added 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (0.60 g, 2.2 mmol) and a solution of (R)-methyl 4-(((1-(2-fluorophenyl)ethyl)amino)methyl)benzoate (250 mg, 0.87 mmol) in DCM (2 mL) followed by DIEA (0.30 mL, 1.74 mmol). The resulting suspension was stirred at rt overnight and diluted with DCM and brine. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 20% EtOAc/DCM) to afford the title compound as a white solid (87 mg, 19%). MS(ESI+) m/z 529.3 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (eluting with 20% EtOAc/DCM)

Sources & evidence

ORD record
ord-687bdaf366394afc97808e0728d91d2d
Source dataset
uspto-grants-2016_05
Patent number
US09345740B2

Reaction notes

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