Diisopropylethylamine → HCID 54754618, compound

HRID 928914Notes

Reaction equation

HRID 928914 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH3:23])[NH:5][C:6](=[O:22])[C@H:7]([CH3:21])[NH:8][C:9](=[O:20])[C@H:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[S:19])[CH3:18])[NH2:11].[N:25]([C:28]1[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=1)=[N+:26]=[N-:27].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH3:23])[NH:5][C:6](=[O:22])[C@H:7]([CH3:21])[NH:8][C:9](=[O:20])[C@H:10]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[S:19])[CH3:18])[NH:11][C:32](=[O:33])[C:31]1[CH:30]=[CH:29][C:28]([N:25]=[N+:26]=[N-:27])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 30341844-Azidobenzoic acidHCID 86678052HCID 86678052, compound

Product 1

HCID 54754618HCID 54754618, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Nε-thioacetyl-lysinyl-alaninyl-alanine methyl ester (50 mg, 0.14 mmol) in 0.8 mL of THF was added a solution of 4-azidobenzoic acid (35 mg, 0.21 mmol) in 0.8 mL of THF. PyBOP (109 mg, 0.21 mmol) and DIPEA (59 mg, 0.42 mmol) were introduced into the reaction mixture. The reaction was stirred at room temperature for 6 h, and then solvent was removed under reduced pressure. Silica gel column chromatography (ethyl acetate: hexanes 10:1) afforded Nα-4-azidobenzoyl-Nε-thioacetyl-lysinyl-alaninyl-alanine methyl ester (58 mg, 0.115 mmol, 82%) as a pale yellow solid. 1H NMR (CD2Cl2, 500 MHz) δ (ppm): 1.39 (s, 3H), 1.40 (s, 3H), 1.47 (m, 2H), 1.67 (m, 2H), 1.88 (m, 2H), 2.87 (s, 3H), 3.57 (m, 2H), 3.68 (s, 3H), 4.41 (m, 1H), 4.46 (m, 1H), 4.64 (m, 1H), 7.05 (d, J=8.6 Hz, 2H), 7.20 (d, J=7.2 Hz, 1H), 7.36 (d, J=6.8 Hz, 1H), 7.44 (d, J=7.0 Hz, 1H), 7.86 (d, J=8.6 Hz, 2H), 8.32 (m, 1H).

Workup

  1. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ca2fe44b04e24d499cf7748549500f07
Source dataset
uspto-grants-2016_03
Patent number
US09290791B2

Reaction notes

Loading…