1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 135890168, compound

HRID 539882Notes

Reaction equation

HRID 539882 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:36][C:37]1[CH:38]=[CH:39][C:40]([O:54][CH2:55][CH2:56][CH3:57])=[C:41]([C:43]2[NH:48][C:47](=[O:49])[C:46]([CH2:50][CH3:51])=[C:45]([CH2:52][CH3:53])[N:44]=2)[CH:42]=1>ClCCl>[CH2:52]([C:45]1[N:44]=[C:43]([C:41]2[CH:42]=[C:37]([NH:36][C:12]([CH2:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])=[O:14])[CH:38]=[CH:39][C:40]=2[O:54][CH2:55][CH2:56][CH3:57])[NH:48][C:47](=[O:49])[C:46]=1[CH2:50][CH3:51])[CH3:53]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 136197415HCID 136197415, compound

Product 1

HCID 135890168HCID 135890168, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Boc-4-aminobutyric acid (203 mg, 1 mmol) was dissolved in dichloromethane (50 ml), and added with EDCI (180 mg, 1 mmol) and HOBT (135 mg, 1 mmol), followed by stirring at room temperature for 12 h. The compound of example 42 (300 mg, 1 mmol) was added thereinto and the stirring continued at room temperature for 6 h. The reaction mixture was washed with water (50 ml) and saturated saline (50 ml) respectively. The organic layer was dried with anhydrous sodium sulfate, and concentrated, and the residue was passed through a silica gel column to give the white title compound (200 mg, yield: 41%). 1H NMR (CDCl3) δ: 9.00 (1H, br), 8.39 (1H, d), 8.09 (1H, dd), 6.99 (1H, d), 4.83 (1H, t), 4.14 (2H, t), 3.27 (2H, m), 2.65 (2H, q), 2.59 (2H, q), 2.41 (2H, t), 1.97 (2H, m), 1.89 (2H, m), 1.48 (9H, s), 1.29 (3H, t), 1.14 (3H, t), 1.13 (3H, t).

Workup

  1. waitthe stirring continued at room temperature for 6 h
  2. washThe reaction mixture was washed with water (50 ml) and saturated saline (50 ml) respectively
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-45337920db6d42a1bc02378d92b7ec19
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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