L-Leucine → N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-L-isoleucyl-L-leucine

HRID 1636223Notes

Reaction equation

HRID 1636223 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:10]([C:19]([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[C@H:11]([C:16](O)=[O:17])[C@H:12]([CH2:14][CH3:15])[CH3:13].C(N(C(C)C)CC)(C)C>CN(C)C=O>[NH:10]([C:19]([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[C@H:11]([C:16]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:17])[C@H:12]([CH2:14][CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 6106L-LeucineHCID 81531DiisopropylethylamineHCID 2724629N-Fmoc-L-isoleucine

Product 1

HCID 71353139N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-L-isoleucyl-L-leucine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acylation of the Leu resin with Fmoc-Ile (1.42 g, 4 mmole) activated with O-(benzotriazol-1-yl),1,1,3,3,-tetramethyluronium hexafluorophosphate (HBTU) (1.52 g, 4 mmole) and diisopropylethylamine (1.4 ml, 8 mmole) in dimethylformamide (8 ml) for 30 minutes. After the reaction, the resin was washed five times (as above) with dimethylformamide to remove the excess reagents and dried. Only half of the Fmoc-Ile-Leu resin thus obtained was used in the next step.

Workup

  1. customAfter the reaction
  2. washthe resin was washed five times (as above) with dimethylformamide
  3. customto remove the excess reagents
  4. customdried

Sources & evidence

ORD record
ord-204eca5b6fc542ccba8d1e330e779273
Source dataset
uspto-grants-2000_03
Patent number
US06034057

Reaction notes

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