2-Thiophenecarboxylic acid → N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-(thiophene-2-carbonyl)amino-L-alanine

HRID 393108Notes

Reaction equation

HRID 393108 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:22]([OH:24])=[O:23])[NH:4][C:5]([O:7][CH2:8][CH:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:6].[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](O)=[O:31].C1C=NC2N(O)N=NC=2C=1.C(N=C=NC(C)C)(C)C>CN1CCCC1=O>[CH:11]1[C:10]2[CH:9]([CH2:8][O:7][C:5]([NH:4][C@H:3]([C:22]([OH:24])=[O:23])[CH2:2][NH:1][C:30]([C:26]3[S:25][CH:29]=[CH:28][CH:27]=3)=[O:31])=[O:6])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 12734DiisopropylcarbodiimideHCID 181649HOAtHCID 688638Fmoc-Dap-OH

Product 1

HCID 68820267N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-(thiophene-2-carbonyl)amino-L-alanine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 3-amino-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine on Wang resin (2 g), thiophene-2-carboxylic acid (1.41 g, 11.0 mmol), HOAT (1.50 g, 11.0 mmol) and diisopropylcarbodiimide (1.68 mL, 10.7 mmol) in N-methylpyrrolidinone (20 mL) was shaken for 3 h and then washed with dichloromethane and methanol to give N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-(thiophene-2-carbonyl)amino-L-alanine on Wang resin. The Fmoc group was cleaved by treatment with 25% piperidine in N-methylpyrrolidinone, followed by shaking for 1 h. The resin was washed with dichloromethane and methanol to give 3-(thiophene-2-carbonyl)amino-L-alanine on Wang resin.

Workup

  1. washwashed with dichloromethane and methanol

Sources & evidence

ORD record
ord-f1e46cc280464c8ca5feed9ec7ba786d
Source dataset
uspto-grants-2004_10
Patent number
US06803384B2

Reaction notes

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