4-Methylmorpholine → HCID 69760119, compound

HRID 990916Notes

Reaction equation

HRID 990916 reaction equation
[CH2:1]([O:8][C:9](C1CCCCC1(N)C(O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][CH:23]([CH:26]1[CH2:28][CH2:27]1)[C:24]#[N:25].O[N:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2N=N1.CN1CC[O:43][CH2:42]C1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:10])[NH:30][CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH:33]1[C:42](=[O:43])[NH:22][CH:23]([C:24]#[N:25])[CH:26]1[CH2:28][CH2:27]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 184170202-amino-2-cyclopropylacetonitrile hydrochlorideHCID 69759728HCID 69759728, compound

Product 1

HCID 69760119HCID 69760119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-Benzyloxycarbonyl-amino-cyclohexane carboxylic acid (1.46 g, 5.26 mmol), 2-Amino-2-cyclopropyl-acetonitrile hydrochloride (0.70 g, 5.27 mmol ), 1-hydroxybenzotriazole (0.89 g, 5.82 mmol) and N-methylmorpholine (1.07 g, 10.58 mmol) in DMF is cooled to 0° C. and treated with 1-ethyl-3-(3-dimethylamino)propyl carbodiimide hydrochloride (2.02 g, 10.54 mmol). The reaction mixture is allowed to warm to room temperature overnight and concentrated. The residue is dissolved in CH2Cl2, washed with dilute aqueous HCl and saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated to give a brown oil. This brown oil is purified via flash chromatograhy with hexane:EtOAc 6:1 to 3:1 to give the product as a white foam.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in CH2Cl2
  3. washwashed with dilute aqueous HCl and saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customThis brown oil is purified via flash chromatograhy with hexane:EtOAc 6:1 to 3:1

Sources & evidence

ORD record
ord-85639c91cac64f6489dadffa3edd7ce2
Source dataset
uspto-grants-2002_10
Patent number
US06462076B2

Reaction notes

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