Water → Z-Asn-Leu-OMe

HRID 1580862Notes

Reaction equation

HRID 1580862 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]([NH:21][C@H:22]([C:27](OC2C=CC([N+]([O-])=O)=CC=2)=[O:28])[CH2:23][C:24]([NH2:26])=[O:25])=[O:20])=[CH:13][CH:12]=1.O>CN(C)C=O>[NH:21]([C:19]([O:18][CH2:17][C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1)=[O:20])[C@H:22]([C:27]([NH:1][C@H:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:28])[CH2:23][C:24](=[O:25])[NH2:26]

Participants

5

Reactant 3

HCID 962WaterHCID 65105(+)-L-Leucine methyl esterHCID 7021351Z-Asn-onp

Product 1

HCID 12814329Z-Asn-Leu-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.7 g of H-Leu-OMe and 46.0 g of Z-Asn-ONP are dissolved in 100 ml of freshly distilled dimethylformamide. The solution is allowed to stand for 19 hours at 25°C. Thereafter 1.2 liters of water are added and the crystalline precipitate is filtered off. The dipeptide derivative is dried at 40°C in vacuo and is then twice recrystallised from methanol-water. Melting point 180°-181°C; [α]20D = + 9° (c = 2.05 in chloroform).

Workup

  1. filtrationthe crystalline precipitate is filtered off
  2. dry with materialThe dipeptide derivative is dried at 40°C in vacuo
  3. customis then twice recrystallised from methanol-water
  4. custom[α]20D = + 9° (c = 2.05 in chloroform)

Sources & evidence

ORD record
ord-642599e48eae405bb114e7ab1a493627
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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