Z-Trp-NH(CH2)4NHBoc → Trp-NH(CH2)4NHBoc

HRID 2074348Notes

Reaction equation

HRID 2074348 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1>CO.CN(C=O)C.[Pd]>[NH2:1][C@H:2]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

4

Reactant 1

HCID 16735216Z-Trp-NH(CH2)4NHBoc

Product 1

HCID 16735218Trp-NH(CH2)4NHBoc

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

Same procedure as above with Z-Trp-NH(CH2)4NHBoc (1.16 g, 2.28 mmol), 10% Pd/C (242 mg) in MeOH/DMF (10 mL, 1/1). After purification by flash chromatography on silica gel (4-25% MeOH/CH2Cl2), Trp-NH(CH2)4NHBoc was isolated as a white foam (701 mg, 82%). 1H NMR (300 MHz, CDCl3) δ 1.39 (m, 4H, 2 CH2), 1.46 (s, 9H, (CH3)3), 3-3.35 (m, 6H, CH2 Trp, 2 CH2N), 3.7 (m, 1H, CHα), 4.71 (m, 1H, NHBoc), 7.05 (d, J=2 Hz, 1 aromatic H), 7.1 (t, J=7.7 Hz, 1 aromatic H), 7.2 (m, 2H, 1 aromatic H, NH amide), 7.38 (d, J=7.9 Hz, 1 aromatic H), 7.65 (d, J=7.9 Hz, 1 aromatic H), 8.94 (broad s, 1H, NH indole). 13C NMR (75 MHz, CDCl3) δ 26.9, 27.6, 30.8 (2 CH2, CH2 Trp), 28.5 ((CH3)3), 38.7, 40.3 (CH2NHCO, CH2NHBoc), 55.6 (CHα), 79.3 (C(CH3)3), 111.3, 111.4, 118.9, 119.5, 122, 123.3, 127.6, 136.4 (8 aromatic C), 156.2 (CO carbamate), 174.8 (CO amide).

Workup

  1. customAfter purification by flash chromatography on silica gel (4-25% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-3760ef36d1ef46f4983230610830ca01
Source dataset
uspto-grants-2011_04
Patent number
US07919468B2

Reaction notes

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