Fmoc-leucine → Fmoc-Leu-Leu-OBzl

HRID 537624Notes

Reaction equation

HRID 537624 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:17]([C:26]([O:28][CH2:29][CH:30]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[C@H:18]([C:23](O)=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21].CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl.C1C=CC2N(O)N=NC=2C=1>[NH:17]([C:26]([O:28][CH2:29][CH:30]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]2[C:31]1=[CH:32][CH:33]=[CH:34][CH:35]=2)=[O:27])[C@H:18]([C:23]([NH:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 1549133Fmoc-leucineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6451313Benzyl L-leucinate

Product 1

HCID 102027077Fmoc-Leu-Leu-OBzlYield 93%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 6212ChloroformSolvent

Procedure

The obtained wet crystals of Leu-OBzl (2-MeO-4-OC12OC22) were dissolved in chloroform (13 mL), Fmoc-Leu-OH (373 mg, 1.06 mmol) and HOBt (14.3 mg, 106 μmol) were added at room temperature, and EDC.HCl (223 mg, 1.16 mmol) was further added under ice-cooling. The mixture was warmed to room temperature, stirred overnight, and concentrated under reduced pressure. Methanol (10 mL) was added to the residue, and the precipitate was collected by filtration to give Fmoc-Leu-Leu-OBzl (2-MeO-4-OC12OC22) (1.02 g, 93% yield relative to Bzl (2-MeO-4-OC12OC22)OH).

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. additionMethanol (10 mL) was added to the residue
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-fcb3b9c21c31471494c44a946f60c6b2
Source dataset
uspto-grants-2014_10
Patent number
US08859732B2

Reaction notes

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