Triethylamine → HCID 87576227, compound

HRID 1943325Notes

Reaction equation

HRID 1943325 reaction equation
[O:1]=[C:2]([C@@:24]1([OH:65])[CH2:41][C@H:40]([O:42][C@@H:43]2[O:57][C@@H:56]([CH3:58])[C@H:46]3[O:47][C@H:48]4[N:53]([C@H:45]3[CH2:44]2)[CH2:52][CH2:51][O:50][C@@H:49]4[O:54][CH3:55])[C:39]2[C:26](=[C:27]([OH:64])[C:28]3[C:29](=[O:63])[C:30]4[C:35]([C:36](=O)[C:37]=3[C:38]=2[OH:59])=[C:34]([O:61][CH3:62])[CH:33]=[CH:32][CH:31]=4)[CH2:25]1)[CH2:3][O:4][CH:5]1[O:10][CH:9]([CH2:11][O:12][CH2:13][C:14]([O:16]N2C(=O)CCC2=O)=O)[CH2:8][CH2:7][CH2:6]1.F[C:67](F)(F)C(O)=O.[NH2:73][CH2:74][CH2:75][N:76]1[C:80](=[O:81])[CH:79]=[CH:78][C:77]1=[O:82].C(N(CC)CC)C>ClCCl>[O:82]=[C:77]1[CH:78]=[CH:79][C:80](=[O:81])[N:76]1[CH2:75][CH2:74][NH:73][C:14](=[O:16])[CH2:13][O:12][CH2:11][CH:9]1[CH2:8][CH2:7][CH2:6][CH:5]([O:4][CH2:3][C:2](=[O:1])[C@@:24]2([OH:65])[CH2:41][C@H:40]([O:42][C@@H:43]3[O:57][C@@H:56]([CH3:58])[C@H:46]4[O:47][C@H:48]5[N:53]([C@H:45]4[CH2:44]3)[CH2:52][CH2:51][O:50][C@@H:49]5[O:54][CH3:55])[C:39]3[C:26](=[C:27]([OH:64])[C:28]4[C:29](=[O:63])[C:30]5[C:35]([C:36](=[CH2:67])[C:37]=4[C:38]=3[OH:59])=[C:34]([O:61][CH3:62])[CH:33]=[CH:32][CH:31]=5)[CH2:25]2)[O:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16212752Trifluoroacetic acid--1-(2-aminoethyl)-1H-pyrrole-2,5-dione (1/1)HCID 44603532HCID 44603532, compound

Product 1

HCID 87576227HCID 87576227, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude intermediate 50 (103.8 mg) in anhydrous dichloromethane (29.7 ml) under argon atmosphere, the commercially available N-(2-aminoethyl)maleimide trifluoroacetate salt (57.9 mg, 0.228 mmol) and anhydrous triethylamine (23.1 mg, 0.228 mmol) were added. The reaction mixture was stirred at room temperature for 1 h, until disappearance of the starting material (HPLC-MS analysis). The solvent was evaporated under vacuum and the residue rinsed with a mixture of Et2O/n-hexane (1 ml/20 ml). The crude was then purified by flash column chromatography (EtOH:CH2Cl2=0.2:9.8) on silica gel (230-400 mesh), affording 12.2 mg (red solid, yield calculated on PNU-159682=20%) of 51 as a diasteroisomeric mixture. MS (ESI): 936 [M+H]+. Retention time=5.86, according to the following method:

Workup

  1. customThe solvent was evaporated under vacuum
  2. washthe residue rinsed with a mixture of Et2O/n-hexane (1 ml/20 ml)
  3. customThe crude was then purified by flash column chromatography (EtOH:CH2Cl2=0.2:9.8) on silica gel (230-400 mesh)
  4. customaffording

Sources & evidence

ORD record
ord-2a7e93ce8d6d44e697996de3f2851b70
Source dataset
uspto-grants-2013_03
Patent number
US08389697B2

Reaction notes

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