Triethylamine → HCID 68226450, compound

HRID 1952584Notes

Reaction equation

HRID 1952584 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:37])[CH:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:26](=[O:36])[NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[CH:20][C:21]=1[C:22]([F:25])([F:24])[F: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:79]1[CH:83]=[CH:82][CH:81]=[C:80]1[C:84](O)=[O:85]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:37])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:26](=[O:36])[NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[CH:20][C:21]=1[C:22]([F:25])([F:23])[F:24])=[O:16])[CH2:12][NH:13][C:84]([C:80]1[S:79][CH:83]=[CH:82][CH:81]=1)=[O:85]

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 86671261HCID 86671261, compound

Product 1

HCID 68226450HCID 68226450, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of S)-3-Amino-2-{[5-(3-hydroxy-benzylcarbamoyl)-3-trifluoromethylthiophene-2-carbonyl]-amino}-propionic acid methyl ester trifluoro-acetic acid salt (0.34 mmol) in anhydrous DMF (5 mL) was added triethylamine (0.14 mL, 1.02 mmol), HBTU (0.19 g, 0.51 mmol), HOBT (0.055 g, 0.41 mmol), and 2-Thiophenecarboxylic acid (0.048 g, 0.37 mmol). The mixture was stirred at room temperature 1.5 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 (61%) colorless oil product. MS m/e 556.0 (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-61dbf8036bb84fc28083bfe968413809
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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