Fmoc-succinimide → N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-[(2,4,6-trimethoxyphenyl)methyl]-L-glutamine

HRID 2107850Notes

Reaction equation

HRID 2107850 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[C:16]([O:22][CH3:23])[C:4]=1[CH2:5][NH:6][C:7](=[O:15])[CH2:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11].[C:24](C1CC(=O)NC1=O)([O:26][CH2:27][CH:28]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25]>C(Cl)(Cl)Cl.CO.C(O)(=O)C>[NH:11]([C:24]([O:26][CH2:27][CH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[C:40]1=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:25])[C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][CH2:8][C:7](=[O:15])[NH:6][CH2:5][C:4]1[C:3]([O:2][CH3:1])=[CH:19][C:18]([O:20][CH3:21])=[CH:17][C:16]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 9883579Fmoc-succinimideHCID 14836422N'(2,4,6-trimethoxybenzyl)-L-glutamine

Product 1

HCID 14442897N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-[(2,4,6-trimethoxyphenyl)methyl]-L-glutamine

Reagents, catalysts & solvents 1

HCID 21866353chloroform methanol HOAcSolvent

Procedure

N'(2,4,6-trimethoxybenzyl)-L-glutamine (0.97 g, 3 mmol) was reacted with Fmoc-succinimide as described in Step 3 of Example 1 to give 1.23 g (78%), thin layer chromatography 1 spot Rf 0.35 chloroform/methanol/acetic acid (90:5:5).

Sources & evidence

ORD record
ord-23f3d8147de0416e874c9332bada9a55
Source dataset
uspto-grants-1990_06
Patent number
US04935536

Reaction notes

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