4-Methylmorpholine → 2-(2-Tert-butoxycarbonylamino-4-phenyl-butyrylamino)-3-methylbutyric acid methyl ester

HRID 2197257Notes

Reaction equation

HRID 2197257 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:33]([NH:40][C@H:41]([C:50](O)=[O:51])[CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34].CN1CCOCC1>CN(C=O)C>[CH3:2][O:3][C:4](=[O:10])[CH:5]([NH:6][C:50](=[O:51])[CH:41]([NH:40][C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[CH2:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH:7]([CH3:9])[CH3:8]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acidHCID 11984198Methyl D-valinate hydrochloride

Product 1

HCID 666609682-(2-Tert-butoxycarbonylamino-4-phenyl-butyrylamino)-3-methylbutyric acid methyl esterYield 142.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cooled solution of D-valine methyl ester hydrochloride (1000 mg, 3.58 mmol) and HOBt (in DMF (14 mL) was added EDCl (755 mg, 3.94 mmol). After the mixture was stirred for 30 min, N-boc-L-homophenylalanine (600 mg, 3.58 mmol) and N-methylmorpholine (1 mL, 8.95 mmol) were added. The mixture was warmed to room temperature and stirred overnight. The solvent was removed and the residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic phases were dried over anhydrous Na2SO4. After concentration under reduced pressure, the crude title compound (2000 mg) was obtained and used in the next step without further purification.

Workup

  1. stirringstirred overnight
  2. customThe solvent was removed
  3. customthe residue was partitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic phases were dried over anhydrous Na2SO4
  6. concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record
ord-971182d299ba41eda21098de8fd8246b
Source dataset
uspto-grants-2012_12
Patent number
US08338471B2

Reaction notes

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