Triethylamine → HCID 131717864, compound

HRID 1590962Notes

Reaction equation

HRID 1590962 reaction equation
[NH2:1][C@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].C(N(CC)CC)C.[NH:25]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C@H:26]([C:37]([O:39]N1C(=O)CCC1=O)=[O:38])[C@@H:27]([CH3:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(#N)C>[CH3:36][C@@H:27]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@H:26]([NH:25][C:47]([O:49][C:50]([CH3:52])([CH3:53])[CH3:51])=[O:48])[C:37]([OH:39])=[O:38].[NH2:1][C@H:2]([C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:6])[OH:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7009632(4S)-4-amino-5-benzyloxy-5-oxo-pentanoic acidHCID 12879029Boc-Thr(Bzl)-OSu

Product 1

HCID 131717864HCID 131717864, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.83 g of H-Glu-OBzl dissolved in 40 ml of acetonitrile were added 3.3 ml of triethylamine and 5.00 g of Boc-Thr(Bzl)-OSu under ice-cooling. The mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate and the resulting solution was washed with 30 ml of water twice. The ethyl acetate layer was dried with anhydrous magnesium sulfate. The solvent was removed by distillation to dry the ethyl acetate layer, whereby 5.50 g (yield: 87.2%) of the above objective compound was obtained as a powder form product.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 50 ml of ethyl acetate
  4. washthe resulting solution was washed with 30 ml of water twice
  5. dry with materialThe ethyl acetate layer was dried with anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation
  7. dry with materialto dry the ethyl acetate layer

Sources & evidence

ORD record
ord-0c5d9703500a43a5b5b338648344c05e
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Reaction notes

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