Triethylamine → HCID 68226629, compound

HRID 1952619Notes

Reaction equation

HRID 1952619 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:36])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:25](=[O:35])[NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)=[CH:20][C:21]=1[CH:22]([CH3:24])[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:78]1[CH:82]=[CH:81][CH:80]=[C:79]1[C:83](O)=[O:84]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:36])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:25](=[O:35])[NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)=[CH:20][C:21]=1[CH:22]([CH3:24])[CH3:23])=[O:16])[CH2:12][NH:13][C:83]([C:79]1[S:78][CH:82]=[CH:81][CH:80]=1)=[O:84]

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 68226547HCID 68226547, compound

Product 1

HCID 68226629HCID 68226629, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-{[5-(3-hydroxy-benzylcarbamoyl)-3-isopropyl-thiophene-2-carbonyl]-amino}-propionic acid methyl ester trifluoro-acetic acid salt (0.16 mmol) in anhydrous DMF (4 mL) was added triethylamine (0.07 mL, 0.48 mmol), HBTU (0.091 g, 0.24 mmol), HOBT (0.026 g, 0.19 mmol), and 2-Thiophenecarboxylic acid (0.025 g, 0.19 mmol). The mixture was stirred at room temperature 1.5 h, treated with EtOAc (30 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (0-100% EtOAc in hexane) to give 0.040 g (47%) white foam product. MS m/e 530.0 (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 (0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-41d8b5fce61443b3becfef6848e20455
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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