Triethylamine → HCID 131711692, compound

HRID 2052270Notes

Reaction equation

HRID 2052270 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@@H:18]([C:25]([NH2:27])=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:11][C:12](=[O:14])[OH:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C(N(CC)CC)C.[NH:35]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C@H:36]([C:47](ON1C(=O)CCC1=O)=[O:48])[CH2:37][C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[NH:40][CH:39]=1>CN(C=O)C>[NH:35]([C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C@H:36]([C:47]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@@H:18]([C:25]([NH2:27])=[O:26])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH2:11][C:12](=[O:13])[OH:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:48])[CH2:37][C:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[NH:40][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98767tert-Butyl (S)-(2-((2,5-dioxo-1-pyrrolidinyl)oxy)-1-(1H-indol-3-ylmethyl)-2-oxoethyl)carbamateHCID 131711693HCID 131711693, compound

Product 1

HCID 131711692HCID 131711692, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.25 g (5.93 mmoles) of H-Leu-Asp-D-Phg-NH2, prepared as described in Example 5, Step 2, are dissolved in a mixture of 50 ml of DMF and 10 ml of HMFA, and 0.84 ml (5.93 mmoles) of triethylamine and 2.65 g (6.6 mmoles) of BOC-Trp-OSu are added to the solution. The reaction mixture is stirred for 4 hours, whereupon a clear mixture is obtained. The mixture is allowed to stand overnight, and then DMF is evaporated in vacuo. The residual mixture containing HMFA is diluted with water, the obtained suspension is allowed to stand at a cool place, and then the precipitate is filtered off. The resulting crude product, weighing 4.31 g, is boiled twice in ethyl acetate, and the suspension is filtered when hot. 2.87 g (72.8%) of BOC-Trp-Leu-Asp-D-Phg-NH2 are obtained; m.p.: 195°-200° C., Rf5 : 0.55. The product is used in the next step without further purification.

Workup

  1. additionare added to the solution
  2. customis obtained
  3. waitto stand overnight
  4. customDMF is evaporated in vacuo
  5. additionThe residual mixture containing HMFA
  6. additionis diluted with water
  7. filtrationthe precipitate is filtered off
  8. filtrationthe suspension is filtered when hot

Sources & evidence

ORD record
ord-e5a96795d8494e48a500c807dd5b7dbf
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

Loading…