4-Methylmorpholine → HCID 69692725, compound

HRID 1814381Notes

Reaction equation

HRID 1814381 reaction equation
[C:1]([O:5][C:6]([CH2:8][C@H:9]([NH:12][S:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][C:17]=1[O:25][CH2:26][CH2:27][C:28]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[N:33]2)(=[O:15])=[O:14])[C:10]#[N:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:40]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH4+].[OH-]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[CH2:8][C@H:9]([NH:12][S:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](=[O:22])[NH2:40])=[CH:18][C:17]=1[O:25][CH2:26][CH2:27][C:28]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=[N:33]2)(=[O:14])=[O:15])[C:10]#[N:11])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69697981HCID 69697981, compound

Product 1

HCID 69692725HCID 69692725, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acid 4-((S)-2-tert-butoxycarbonyl-1-cyano-ethylsulfamoyl)-3-(2-quinolin-5-yl-ethoxy)-benzoic acid (0.60 g, 1.10 mmol) in THF (20 mL) was added EDCI (0.33 g, 1.70 mmol), HOBt (0.23 g, 1.70 mmol), and N-methylmorpholine (1.70 mmol, 0.20 mL). The reaction was allowed to stirred at room temperature for 1 h then followed by addition of NH4OH (10 mL). The mixture was stirred for another 12 h. To reaction was added EtOAc (100 mL) and washed with the 5% citric acid and then saturated NaHCO3. The organic phase was dried (MgSO4), and then the solvent was removed under vacuum. The resulting crude product was purified using silica gel flash chromatography (70% EtOAc in hexanes). (S)-3-[4-Carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-3-cyano-propionic acid tert-butyl ester was obtained in 22% yield (0.130 g) as an off white foam. MS (APCI) m/z 525.2 (M+1).

Workup

  1. stirringThe mixture was stirred for another 12 h
  2. customTo reaction
  3. washwashed with the 5% citric acid
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customthe solvent was removed under vacuum
  6. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-3168e0b893884982ad4d17349b4af0f3
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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