Triethylamine → N-Cbz-valylprolylglycine methyl ester

HRID 1471297Notes

Reaction equation

HRID 1471297 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([N:18]1[CH2:25][CH2:24][CH2:23][C@H:19]1[C:20](O)=[O:21])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.[CH3:45][O:46][C:47](=[O:50])[CH2:48][NH2:49]>CN(C=O)C.ClCCl>[CH3:45][O:46][C:47](=[O:50])[CH2:48][NH:49][C:20](=[O:21])[C@@H:19]1[CH2:23][CH2:24][CH2:25][N:18]1[C:16](=[O:17])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 122755Glycine methyl ester hydrochlorideHCID 10783923Z-Val-pro-OH2×

Product 1

HCID 67057640N-Cbz-valylprolylglycine methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Cbz-valylproline (Cbz-NH-[VP]-CO2H) (3.5 g, 10 mmol), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide (1.6 g, 11 mmol) and triethylamine (2.0 g, 20 mmol) in DMF (15 mL) is added dropwise a solution of glycine methyl ester hydrochloride (1.38 g, 11 mmol) in DMF (5 mL). The solution is stirred at room temperature and the reaction monitored by TLC until the disappearance of N-Cbz-valylproline. The reaction solution is then diluted with dichloromethane (50 mL) and the organic layer is extracted with 0.1 N HCl (20 mL), water (20 mL), then dried over Na2SO4. The solvent is removed in vacuo to afford the desired compound.

Workup

  1. extractionthe organic layer is extracted with 0.1 N HCl (20 mL), water (20 mL)
  2. dry with materialdried over Na2SO4
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7e333866a41043d4bcd374530e0b00f5
Source dataset
uspto-grants-2015_04
Patent number
US09011918B2

Reaction notes

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