Triethylamine → Z-Ile-Leu-Leu-Ala-Gln-OH

HRID 1632388Notes

Reaction equation

HRID 1632388 reaction equation
[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:2]([C:7]([O:9]N1C(=O)CCC1=O)=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].[NH2:27][C@H:28]([C:33]([NH:35][C@H:36]([C:41]([NH:43][C@H:44]([C:46]([NH:48][C@H:49]([C:55]([OH:57])=[O:56])[CH2:50][CH2:51][C:52](=[O:54])[NH2:53])=[O:47])[CH3:45])=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31].C(N(CC)CC)C>CN(C)C=O>[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])[C@H:2]([C:7]([NH:27][C@H:28]([C:33]([NH:35][C@H:36]([C:41]([NH:43][C@H:44]([C:46]([NH:48][C@H:49]([C:55]([OH:57])=[O:56])[CH2:50][CH2:51][C:52](=[O:54])[NH2:53])=[O:47])[CH3:45])=[O:42])[CH2:37][CH:38]([CH3:39])[CH3:40])=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31])=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13361528Z-Ile-OSuHCID 131713837H-Leu-Leu-Ala-Gln-OH

Product 1

HCID 131713839Z-Ile-Leu-Leu-Ala-Gln-OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.41 Grams of Z-Ile-OSu, the above-obtained H-Leu-Leu-Ala-Gln-OH and 0.36 ml of triethylamine were dissolved in 50 ml of dimethylformamide, then the mixture was stirred at a room temperature for 20 hours. After removal of dimethylformamide by distillation, 1N-citric acid was added to the residue, and crystals being precipitated were collected by filtration and washed with hot methanol to obtain 1.17 g of Z-Ile-Leu-Leu-Ala-Gln-OH.

Workup

  1. customAfter removal of dimethylformamide
  2. distillationby distillation, 1N-citric acid
  3. additionwas added to the residue, and crystals
  4. custombeing precipitated
  5. filtrationwere collected by filtration
  6. washwashed with hot methanol

Sources & evidence

ORD record
ord-4b90a43f7fe74b4285176cf09f77665d
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

Loading…