4-Methylmorpholine → HCID 178455656, compound

HRID 1355592Notes

Reaction equation

HRID 1355592 reaction equation
[CH2:1]([S:5]([NH:8][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[C:15]([C:17]1[CH:29]=[CH:28][C:20]([CH2:21][NH:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25])=[CH:19][CH:18]=1)#[N:16].Cl.[NH2:31][OH:32].CN1CCOCC1>CO>[CH2:1]([S:5]([NH:8][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4].[OH:32][NH:31][C:15]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][NH:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25])=[CH:28][CH:29]=1)=[NH:16]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 443297Hydroxyamine hydrochlorideHCID 131723948HCID 131723948, compound

Product 1

HCID 178455656HCID 178455656, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product in Example 7 (117 mg, 0.285 mmol) in 1.14 ml methanol was added hydroxylamine hydrochloride (33.7 mg, 0.485 mmol), followed by N-methylmorpholine (53 μl, 0.485 mmol). The reaction mixture was stirred overnight at ambient temperature and then at 50° C. for six hours. The reaction mixture was concentrated in vacuo. The crude product was taken to the next step (Example 9) without further purification. The product eluted at 6.5 minutes by reverse phase (C18) HPLC at 0.1% trifluoroacetic acid in 5-50% aqueous acetonitrile over 20 minutes.

Workup

  1. waitat 50° C. for six hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe crude product was taken to the next step (Example 9) without further purification
  4. washThe product eluted at 6.5 minutes by reverse phase (C18) HPLC at 0.1% trifluoroacetic acid in 5-50% aqueous acetonitrile over 20 minutes

Sources & evidence

ORD record
ord-a90d18d4495a44cd8ce65b39147e9219
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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