Triethylamine → HCID 68226867, compound

HRID 1952592Notes

Reaction equation

HRID 1952592 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:39])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:28](=[O:38])[NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)=[CH:20][C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[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:81]1[CH:85]=[CH:84][CH:83]=[C:82]1[C:86](O)=[O:87]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:39])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:28](=[O:38])[NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)=[CH:20][C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:16])[CH2:12][NH:13][C:86]([C:82]1[S:81][CH:85]=[CH:84][CH:83]=1)=[O:87]

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 68226607HCID 68226607, compound

Product 1

HCID 68226867HCID 68226867, compoundYield 26.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-{[5-(3-hydroxy-benzylcarbamoyl)-3-phenyl-thiophene-2-carbonyl]-amino}-propionic acid methyl ester trifluoro-acetic acid salt (0.27 mmol) in anhydrous DMF (5 mL) was added triethylamine (0.1 mL, 0.81 mmol), HBTU (0.15 g, 0.40 mmol), HOBT (0.044 g, 0.32 mmol), and 2-Thiophenecarboxylic acid (0.038 g, 0.30 mmol). The mixture was stirred at room temperature 1.25 h, treated with EtOAc (50 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (50-80% EtOAc in hexane) to give 0.040 g (26%) colorless oil product. MS m/e 564.0 (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 (50-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-dfcd06650c0e460f81049db0f01e817e
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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