4-Methylmorpholine → HCID 178427303, compound

HRID 1769997Notes

Reaction equation

HRID 1769997 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([OH:29])=O)[CH2:10][CH:11]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:12][NH:13][C:14](=[NH:16])[NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.Cl.[NH2:58][CH2:59][C:60]([O:62]CC)=[O:61].CN1CCOCC1>ClCCl.CC(N(C)C)=O.C(O)(=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:27]([NH:58][CH2:59][C:60]([OH:62])=[O:61])=[O:29])[CH2:10][CH:11]([S:17]([C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)(=[O:18])=[O:19])[CH2:12][NH:13][C:14](=[NH:16])[NH2:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 178427304HCID 178427304, compound

Product 1

HCID 178427303HCID 178427303, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

N-t-Butoxycarbonyl-g-p-toluenesulfonylarginine (10 mmoles), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP, 10 mmoles), ethyl glycinate hydrochloride (13 mmoles) and N-methylmorpholine (50 mmoles) are stirred in a mixture of dichloromethane and dimethylacetamide (1:1, 50 ml) for 2 hr at room temperature. At the end of the reaction time the mixture is acidified with acetic acid, concentrated in vacuo, and the residue taken up in ethyl acetate. The resulting solution is washed with 10% citric acid (3 times), water (2 times), saturated sodium bicarbonate (3 times), water (2 times) and brine (2 times). The organic solution is dried over magnesium sulfate, filtered, dried and concentrated to afford the crude ethyl ester of the title compound. Crystalline material can be obtained from ethyl acetate-hexane mixtures.

Workup

  1. concentrationconcentrated in vacuo
  2. washThe resulting solution is washed with 10% citric acid (3 times), water (2 times), saturated sodium bicarbonate (3 times), water (2 times) and brine (2 times)
  3. dry with materialThe organic solution is dried over magnesium sulfate
  4. filtrationfiltered
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-76d1d6a9793c4feba18ba7d238bd4d9a
Source dataset
uspto-grants-1995_01
Patent number
US05384309

Reaction notes

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