Triethylamine → HCID 68226421, compound

HRID 1952600Notes

Reaction equation

HRID 1952600 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:34])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:23](=[O:33])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[CH:20][C:21]=1[Cl:22])=[O:16])[CH2:12][NH2:13].C(N(CC)CC)C.CCOP(ON1N=NC2C=CC=CC=2C1=O)(OCC)=O.[S:62]1[CH:66]=[CH:65][CH:64]=[C:63]1[C:67](O)=[O:68]>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10](=[O:34])[C@@H:11]([NH:14][C:15]([C:17]1[S:18][C:19]([C:23](=[O:33])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[CH:20][C:21]=1[Cl:22])=[O:16])[CH2:12][NH:13][C:67]([C:63]1[S:62][CH:66]=[CH:65][CH:64]=1)=[O:68]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 107002-Thiophenecarboxylic acidHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 68226620HCID 68226620, compound

Product 1

HCID 68226421HCID 68226421, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-Amino-2-{[3-chloro-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carbonyl]-amino}-propionic acid methylester trifluoro-acetic acid salt (0.59 mmol) in anhydrous DMF (5 mL) was added triethylamine (0.2 mL, 1.18 mmol), DEPBT (0.35 g, 1.18 mmol), and 2-Thiophenecarboxylic acid (0.083 g, 0.65 mmol). The mixture was stirred at room temperature 15 h, treated with EtOAc (100 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 0.15 g (49%) white foam. MS m/e 522.0 (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-c3d72ece6e3c40dfab144d08806f59a4
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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