4-Methylmorpholine → HCID 69266479, compound

HRID 276718Notes

Reaction equation

HRID 276718 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][C@@H:6]([C:23](O)=[O:24])[NH:7][C:8](=[O:22])[CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[CH3:30][O:31][C:32]([C:34]1[CH:35]=[C:36]([CH2:40][O:41][CH2:42][C@@H:43]([C:45]([NH2:47])=[O:46])[NH2:44])[CH:37]=[CH:38][CH:39]=1)=[O:33].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][C@@H:6]([C:23]([NH:47][C:45](=[O:46])[C@H:43]([CH2:42][O:41][CH2:40][C:36]1[CH:37]=[CH:38][CH:39]=[C:34]([C:32]([O:31][CH3:30])=[O:33])[CH:35]=1)[NH2:44])=[O:24])[NH:7][C:8](=[O:22])[CH:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22951559HCID 22951559, compoundHCID 53706240HCID 53706240, compound

Product 1

HCID 69266479HCID 69266479, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanine (1.0 g, 2.68 mmol) and O-[[3-(methoxycarbonyl)phenyl]methyl]-L-serinamide HCl (0.774 g, 2.68 mmol), 1-hydroxybenzotriazole hydrate (0.452 g, 2.95 mmol, and N-methylmorpholine (1.18 mL, 1.085 g, 10.72 mmol) in CH2Cl2 (50 mL) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (0.771 g, 4.02 mmol) in one portion and the mixture is stirred at room temperature for 16 hours. The solution is then washed with 1 N HCl (100 mL), saturated aqueous NaHCO3 (1×50 mL), water (1×50 mL) and brine (1×50 mL), dried over MgSO4, and evaporated. The residual solid is triturated with hot methanol to yield N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-O-[[3-(methoxycarbonyl)phenyl]methyl]-L-serinamide as a white solid.

Workup

  1. washThe solution is then washed with 1 N HCl (100 mL), saturated aqueous NaHCO3 (1×50 mL), water (1×50 mL) and brine (1×50 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residual solid is triturated with hot methanol

Sources & evidence

ORD record
ord-49a24ded18b64da69c0eeae7ee9f3e55
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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