Fmoc isothiocyanate → HCID 59759440, compound

HRID 914512Notes

Reaction equation

HRID 914512 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH:27]1[C:39]2[CH:38]([CH2:40][O:41][C:42]([N:44]=[C:45]=[S:46])=[O:43])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]=2[CH:30]=[CH:29][CH:28]=1>ClCCl>[C:1]([O:5][C:6](=[O:26])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][N:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:45]([NH:44][C:42]([O:41][CH2:40][CH:38]2[C:37]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[C:31]3[C:39]2=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:43])=[S:46])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4154759Fmoc isothiocyanateHCID 597593122-({4-[2-(Heptylamino)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester

Product 1

HCID 59759440HCID 59759440, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-({4-[2-(heptylamino)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester (2.5 g) synthesized in Example 303-2 in dichloromethane (20 mL) was added dropwise 9H-fluorene-9-ylmethyloxycarbonylisothiocyanate (2.5 g), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and subjected to silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1) to give the title compound (3.1 g) as a pale-brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washsubjected to silica gel chromatography (elution solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-8905e9c7db584eb0a5826fabcd5bcf68
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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