Triethylamine → HCID 68226525, compound

HRID 1952653Notes

Reaction equation

HRID 1952653 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:29])[C@@H:5]([NH:8][C:9]([C:11]1[S:12][C:13]([C:18](=[O:28])[NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[CH:14][C:15]=1[C:16]#[N:17])=[O:10])[CH2:6][NH2:7].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:71]1[CH:75]=[CH:74][CH:73]=[C:72]1[C:76](O)=[O:77]>CN(C=O)C.CCOC(C)=O>[CH3:2][O:3][C:4](=[O:29])[C@@H:5]([NH:8][C:9]([C:11]1[S:12][C:13]([C:18](=[O:28])[NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[CH:14][C:15]=1[C:16]#[N:17])=[O:10])[CH2:6][NH:7][C:76]([C:72]1[S:71][CH:75]=[CH:74][CH:73]=1)=[O:77]

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 68226911HCID 68226911, compound

Product 1

HCID 68226525HCID 68226525, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-{[3-cyano-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carbonyl]-amino}-propionic acid methyl ester hydrochloride (0.066 mmol) in anhydrous DMF (5 mL) was added triethylamine (0.03 mL, 0.20 mmol), HBTU (0.030 g, 0.079 mmol), HOBt (0.011 g, 0.079 mmol), and 2-Thiophenecarboxylic acid (0.009 g, 0.069 mmol). The mixture was stirred at room temperature 1.5 h, treated with EtOAc (20 mL), washed with brine, dried over sodium sulfate, filtered and evaporated. The solid residue was purified by column (30-60% EtOAc in hexane) to give 0.0162 g (16%) colorless oil. MS m/e 512.9 (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 (30-60% EtOAc in hexane)

Sources & evidence

ORD record
ord-5bb1a1308d9b4aac9038e60cb19f95e7
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

Loading…