4-Methylmorpholine → HCID 54544565, compound

HRID 2164432Notes

Reaction equation

HRID 2164432 reaction equation
[C:1]([O:5][C:6](=[O:29])[C@H:7]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:8][C:9](=[O:24])[CH:10]([C:21](O)=[O:22])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:41]([O:48][NH2:49])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.CN1CCOCC1>CN(C=O)C>[C:1]([O:5][C:6](=[O:29])[C@H:7]([CH2:25][CH:26]([CH3:28])[CH3:27])[NH:8][C:9](=[O:24])[CH:10]([C:21](=[O:22])[NH:49][O:48][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 102312Benzyloxyamine hydrochlorideHCID 13178375HCID 13178375, compound

Product 1

HCID 54544565HCID 54544565, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The residue from stage (d) was stirred in DMF at -15° C. for 1 hour with HOBT (2 equiv) and DCCl (1 equiv). To the mixture was added a precooled solution of O-benzylhydroxylamine hydrochloride (1 equiv) and NMM (1 equiv) in DMF and stirring continued for 48 hour at +4° C. The product was filtered, the filtrate concentrated in vacuo, dissolved in ethyl acetate and acid/base washed in the normal manner. The solution was dried (MgSO4), evaporated in vacuo and the residue used the next stage without further purification.

Workup

  1. filtrationThe product was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutiondissolved in ethyl acetate
  4. washacid/base washed in the normal manner
  5. dry with materialThe solution was dried (MgSO4)
  6. customevaporated in vacuo
  7. customwithout further purification

Sources & evidence

ORD record
ord-da2c4dc84ed448d7a0279f1dadbc8ce8
Source dataset
uspto-grants-1985_03
Patent number
US04504492

Reaction notes

Loading…