Triethylamine → HCID 68226589, compound

HRID 1952642Notes

Reaction equation

HRID 1952642 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:34])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:23](=[O:33])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[CH:20][C:21]=1[Br:22])=[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:76]1[CH:80]=[CH:79][CH:78]=[C:77]1[C:81](O)=[O:82]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:34])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:23](=[O:33])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[CH:20][C:21]=1[Br:22])=[O:16])[CH2:12][NH:13][C:81]([C:77]1[S:76][CH:80]=[CH:79][CH:78]=1)=[O:82]

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 68226843HCID 68226843, compound

Product 1

HCID 68226589HCID 68226589, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-{[3-bromo-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carbonyl]-amino}-propionic acid methyl ester trifluoro-acetic acid salt (0.26 mmol) in anhydrous DMF (7 mL) was added triethylamine (0.11 mL, 0.78 mmol), HBTU (0.15 g, 0.39 mmol), HOBt (0.042 g, 0.31 mmol), and 2-Thiophenecarboxylic acid (0.050 g, 0.39 mmol). The mixture was stirred at room temperature 15 h, treated with EtOAc (50 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (30-50% EtOAc in hexane) to give 0.0242 g (16%) colorless oil. MS m/e 567.8 (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 (30-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-1e7387145fcb4686aacd5f8c17818cfd
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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