L-Leucine → Boc-Val-Leu

HRID 1381972Notes

Reaction equation

HRID 1381972 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].[NH2:16][C@H:17]([C:22]([OH:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([NH:16][C@H:17]([C:22]([OH:24])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6106L-LeucineHCID 10868DicyclohexylcarbodiimideHCID 83693Boc-L-Valine

Product 1

HCID 6999299Boc-Val-Leu

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 25 ml of a solution of 0.35 g of Boc-Val-OH in methylene chloride the H-Leu-resin described above was added and 5 ml of a solution of 0.33 g of DCC in methylene chloride was then added to the resulting mixture. The mixture was reacted at room temperature for 2 hours. After washing the resin 6 times with 30 ml of methylene chloride, the resin was added to 25 ml of a methylene chloride solution of 0.35 g of Boc-Val-OH and 0.55 g of 1-hydroxybenzotriazole. Then, 5 ml of a methylene chloride solution of 0.33 g of DCC was added thereto and the resulting mixture was again reacted in a similar manner (double coupling). The resin was thoroughly washed with methylene chloride to obtain Boc-Val-Leu-resin.

Workup

  1. additionabove was added
  2. customThe mixture was reacted at room temperature for 2 hours
  3. washAfter washing the resin 6 times with 30 ml of methylene chloride
  4. additionthe resin was added to 25 ml of a methylene chloride solution of 0.35 g of Boc-Val-OH and 0.55 g of 1-hydroxybenzotriazole
  5. additionThen, 5 ml of a methylene chloride solution of 0.33 g of DCC was added
  6. customthe resulting mixture was again reacted in a similar manner (double coupling)
  7. washThe resin was thoroughly washed with methylene chloride

Sources & evidence

ORD record
ord-c01b8e89417a46f895ee733dcce9057a
Source dataset
uspto-grants-1989_02
Patent number
US04804746

Reaction notes

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