Triethylamine → HCID 10160216, compound

HRID 1609879Notes

Reaction equation

HRID 1609879 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[S:9][CH:10]=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][NH2:20])=[O:7].C(N(CC)CC)C.[CH2:29]([O:36][C:37](OC1CC(=O)NC1=O)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[CH3:1][CH:2]([CH3:21])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[S:9][CH:10]=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][NH:20][C:37](=[O:38])[O:36][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22140026HCID 22140026, compoundHCID 86591756HCID 86591756, compound

Product 1

HCID 10160216HCID 10160216, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

27 mg (0.09 mmol) of 3-(2-aminomethylphenyl)thiophene-2-carboxylic acid (3-methylbutyl)amide were dissolved in 3 ml of dry dichloromethane, and the solution was treated with 10 mg (0.1 mmol) of triethylamine and 24 mg (0.1 mmol) of benzyloxycarbonyloxysuccinimide. After a reaction time of 18 h, the mixture was diluted with 20 ml of dichloromethane, washed with saturated NaHCO3 solution and the organic phase was dried and concentrated. After purification by RP-HPLC, 27 mg (70%) of a colorless substance were obtained. MS (ES+): m/z=437 (M+1). 1H-NMR (CDCl3): δ=7.54-7.24 (10H, m), 6.90 (1H, d, J=4.8 Hz), 5.52 (1H, br s), 5.05 (3H, br s), 4.17 (2H, d, J=6.2 Hz), 3.16 (2H, m), 1.14 (1H, m), 1.07 (2H, q, J=7.0 Hz), 0.73 (6H, d, J=6.2 Hz).

Workup

  1. washwashed with saturated NaHCO3 solution
  2. customthe organic phase was dried
  3. concentrationconcentrated
  4. customAfter purification by RP-HPLC, 27 mg (70%) of a colorless substance
  5. customwere obtained

Sources & evidence

ORD record
ord-2bfe4bde728a44c2acfe89fd1d1ce638
Source dataset
uspto-grants-2006_01
Patent number
US06982279B2

Reaction notes

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