Triethylamine → HCID 68226934, compound

HRID 1952580Notes

Reaction equation

HRID 1952580 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:26](=[O:38])[NH:27][CH2:28][C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][NH:33]3)=[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: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:26](=[O:38])[NH:27][CH2:28][C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH:31]=[CH:32][NH:33]3)=[CH:20][C:21]=1[C:22]([F:24])([F:25])[F:23])=[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 86671259HCID 86671259, compound

Product 1

HCID 68226934HCID 68226934, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-({5-[(1H-indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carbonyl}-amino)-propionic acid methyl ester trifluoro-acetic acid salt (0.32 g, 0.49 mmol) in anhydrous DMF (10 mL) was added triethylamine (0.20 mL, 1.47 mmol), HBTU (0.28 g, 0.74 mmol), HOBT (0.079 g, 0.59 mmol), and 2-Thiophenecarboxylic acid (0.069 g, 0.54 mmol). The mixture was stirred at room temperature 2 h, treated with EtOAc (100 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (0-80% EtOAc in hexane) to give 0.172 g (61%) colorless oil product. MS m/e 579.0 (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 (0-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-078990bb5dcf47a4a9710d12b09f4c8c
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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