4-Methylmorpholine → Ethyl N-(1-((benzyloxy)carbonyl)-L-prolyl)-L-leucinate

HRID 1733664Notes

Reaction equation

HRID 1733664 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:20]([O:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:25])[CH3:21].CN1CCOCC1.O=C1C2C=CC=CC=2N=NN1OS(C)(=O)=O>C(Cl)(Cl)Cl.C(OCC)(=O)C.O>[CH2:20]([O:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH:25][C:13](=[O:15])[C@@H:12]1[CH2:16][CH2:17][CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH3:21]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 101987Benzyloxycarbonyl-L-prolineHCID 11658447L-Leucine, ethyl ester, hydrochloride (1:1)HCID 218962814-Oxo-3,4-dihydro-3-methanesulfonyloxy-1,2,3-benzotriazine

Product 1

HCID 6453075Ethyl N-(1-((benzyloxy)carbonyl)-L-prolyl)-L-leucinateYield 66.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Benzyloxycarbonyl-L-proline (1.25 g), L-leucine ethyl ester hydrochloride (1.00 g) and N-methylmorpholine (1.10 ml) are dissolved in chloroform (10 ml) and thereto is added 4-oxo-3,4-dihydro-3-methanesulfonyloxy-1,2,3-benzotriazine (1.20 g). After allowing to stand overnight, to the mixture are added water and ethyl acetate. The ethyl acetate layer is washed and dried, and then the solvent is distilled off to give N-(N-benzyloxycarbonyl-L-prolyl)-L-leucine ethyl ester (1.3 g), melting point: 65°-67° C.

Workup

  1. washThe ethyl acetate layer is washed
  2. customdried
  3. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-89cf0924f3e74005978288a0de1fd424
Source dataset
uspto-grants-1980_12
Patent number
US04242507

Reaction notes

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