Water → HCID 131729981, compound

HRID 2061329Notes

Reaction equation

HRID 2061329 reaction equation
[C:1]([NH:18][C@H:19]([C:30]([OH:32])=[O:31])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[N+:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[S:42]Cl)([O-:35])=[O:34].C(OCC)C.O>O1CCOCC1.CC#N>[NH:18]([C:1]([O:3][CH2:4][CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:2])[C@H:19]([C:30]([OH:32])=[O:31])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][C:22]=1[S:42][C:37]1[C:36]([N+:33]([O-:35])=[O:34])=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 243192-Nitrobenzenesulfenyl chlorideHCID 978343Fmoc-L-tryptophan

Product 1

HCID 131729981HCID 131729981, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2.0 g (4.7 mmole) Fmoc-L-tryptophan in 12 ml dioxane, 0.87 g (4.6 mmole) of 2-nitrophenyl-sulfenylchloride (2-Nps-Cl) in 25 ml dioxane was added under stirring at room temperature. After standing for 3 days, 50 ml ethyl ether was added to the reaction mixture and the solvent was evaporated. The product was purified by chromatography on silica gel in solvent A (Solvent A=Chloroform:Ethanol:Neptane—1:1:1). Rf 0.43. After purification the product was obtained as a yellow-brown crystalline compound. The yield was 2.5 g (89%). HPLC (C18): tR 8.3 min, 85-100% B in 20 min. (A: H2O+0.1% TFA; B: CH3CN+0.1% TFA).

Workup

  1. customthe solvent was evaporated
  2. customThe product was purified by chromatography on silica gel in solvent A (Solvent A=Chloroform:Ethanol:Neptane—1:1:1)
  3. customAfter purification the product
  4. customwas obtained as a yellow-brown crystalline compound

Sources & evidence

ORD record
ord-28061cccaf6b472aa2aa1e3429ca7c83
Source dataset
uspto-grants-2012_10
Patent number
US08283315B2

Reaction notes

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