Fluorenylmethyloxycarbonyl isothiocyanate → 9H-fluoren-9-ylmethyl ({[(1S*,2R*,4S*)-1-(2-fluorophenyl)-2-(hydroxymethyl)-4-methoxycyclopentyl]amino}carbonothioyl)carbamate

HRID 1842193Notes

Reaction equation

HRID 1842193 reaction equation
[NH2:1][C@@:2]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])[CH2:6][C@@H:5]([O:7][CH3:8])[CH2:4][C@H:3]1[CH2:9][OH:10].[C:18]1([CH2:31][O:32][C:33]([N:35]=[C:36]=[S:37])=[O:34])[C:30]2[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1>ClCCl>[F:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C@:2]1([NH:1][C:36]([NH:35][C:33](=[O:34])[O:32][CH2:31][CH:18]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:30][C:29]=3[C:28]3[C:27]2=[CH:26][CH:25]=[CH:24][CH:23]=3)=[S:37])[CH2:6][C@@H:5]([O:7][CH3:8])[CH2:4][C@H:3]1[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 22346806Fluorenylmethyloxycarbonyl isothiocyanateHCID 57827758[(1R*,2S*,4S*)-2-amino-2-(2-fluorophenyl)-4-methoxycyclopentanyl]methanol

Product 1

HCID 578277249H-fluoren-9-ylmethyl ({[(1S*,2R*,4S*)-1-(2-fluorophenyl)-2-(hydroxymethyl)-4-methoxycyclopentyl]amino}carbonothioyl)carbamateYield 67.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(1R*,2S*,4S*)-2-amino-2-(2-fluorophenyl)-4-methoxycyclopentanyl]methanol (225 mg) and fluorenylmethyloxycarbonyl isothiocyanate (316 mg) in dichloromethane (18 mL) was stirred at room temperature for three days. The reaction solution was purified by silica gel column chromatography to obtain the title compound (330 mg).

Workup

  1. customThe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53568e5b1b4f49eca2be0a136722acbb
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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