Triethylamine → HCID 68226780, compound

HRID 1952631Notes

Reaction equation

HRID 1952631 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:35])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:24](=[O:34])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)=[CH:20][C:21]=1[CH2:22][CH3:23])=[O:16])[CH2:12][NH2:13].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[S:77]1[CH:81]=[CH:80][CH:79]=[C:78]1[C:82](O)=[O:83]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:35])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:24](=[O:34])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)=[CH:20][C:21]=1[CH2:22][CH3:23])=[O:16])[CH2:12][NH:13][C:82]([C:78]1[S:77][CH:81]=[CH:80][CH:79]=1)=[O:83]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 107002-Thiophenecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68226822HCID 68226822, compound

Product 1

HCID 68226780HCID 68226780, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-{[3-ethyl-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carbonyl]-amino}-propionic acid methyl ester trifluoro-acetic acid salt (0.46 mmol) in anhydrous DMF (10 mL) was added triethylamine (0.19 mL, 1.38 mmol), HBTU (0.26 g, 0.69 mmol), HOBT (0.074 g, 0.55 mmol), and 2-Thiophenecarboxylic acid (0.071 g, 0.55 mmol). The mixture was stirred at room temperature 15 h, treated with EtOAc (30 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (30-60% EtOAc in hexane) to give 0.0747 g (31%) white foam product. MS m/e 516.0 (M+H+).

Workup

  1. washwashed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe solid residue was purified by column (30-60% EtOAc in hexane)

Sources & evidence

ORD record
ord-66d9a02fc05942a8a8eab12fa305c6b6
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

Loading…