Diisopropylethylamine → HCID 131731089, compound

HRID 1912375Notes

Reaction equation

HRID 1912375 reaction equation
[NH2:1][C@H:2]([C:19]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:6][CH:5]=1.[NH:31]([N:43]=[N+:44]=[N-:45])[C@H:32]([C:40](O)=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CC(=O)OCC>[NH:31]([N:43]=[N+:44]=[N-:45])[C@H:32]([C:40]([NH:1][C@H:2]([C:19]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])=[O:20])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[CH:8][CH:9]=1)=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66669689HCID 66669689, compoundHCID 131731088HCID 131731088, compound

Product 1

HCID 131731089HCID 131731089, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

H-Phe(4-CH2NHBoc)-Leu-OMe 80 (68 mg, 161 μmol, 1 equiv.) was dissolved in DCM (5 ml) and N3-Phe-OH (37 mg, 193 μmol, 1.2 equiv.), HBTU (79 mg, 209 μmol, 1.3 equiv.) and DiPEA (67 μl, 403 μmol, 2.5 equiv.) were added and the mixture was stirred for 90 minutes before being washed with 1M HCl (2×), sat aq. NaHCO3 (3×) and dried over Na2SO4. Column chromatography (10% EA:tol->35% EA:tol) yielded the title compound (71 mg, 119 μmol, 74%). 1H NMR (400 MHz, CDCl3): δ ppm 7.40-7.20 (m, 5H), 7.17 (d, J=7.8 Hz, 2H), 7.04 (d, J=7.9 Hz, 2H), 6.97 (d, J=8.1 Hz, 1H), 6.34 (d, J=7.5 Hz, 1H), 4.93 (s, 1H), 4.67 (dd, J=14.3, 7.1 Hz, 1H), 4.51 (td, J=8.2, 5.4 Hz, 1H), 4.26 (d, J=5.2 Hz, 2H), 4.16 (dd, J=8.2, 4.2 Hz, 1H), 3.70 (s, 3H), 3.24 (dd, J=14.1, 4.1 Hz, 1H), 3.08-2.82 (m, 3H), 1.62-1.46 (m, 3H), 1.45 (s, 9H), 0.88 (d, J=6.1 Hz, 6H). 13C NMR (101 MHz, CDCl3): δ ppm 172.71, 169.82, 168.38, 155.80, 137.63, 135.83, 135.00, 129.51, 129.42, 128.60, 127.81, 127.24, 79.36, 65.13, 54.03, 52.25, 50.80, 44.37, 41.36, 38.33, 37.89, 28.33, 24.70, 22.58, 21.91.

Workup

  1. washbefore being washed with 1M HCl (2×)
  2. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-027d9a3b9bba474c859c852844646b74
Source dataset
uspto-grants-2013_12
Patent number
US08609610B2

Reaction notes

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