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

HRID 1842085Notes

Reaction equation

HRID 1842085 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>[CH:26]1[C:27]2[CH:18]([CH2:31][O:32][C:33](=[O:34])[NH:35][C:36]([NH:1][C@@:2]3([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[F:17])[CH2:6][C@H:5]([O:7][CH3:8])[CH2:4][C@H:3]3[CH2:9][OH:10])=[S:37])[C:30]3[C:29](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:28]=2[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 22346806Fluorenylmethyloxycarbonyl isothiocyanateHCID 57827534[(1R*,2S*,4R*)-2-amino-2-(2-fluorophenyl)-4-methoxycyclopentyl]methanol

Product 1

HCID 578275719H-fluoren-9-ylmethyl ({[(1S*,2R*,4R*)-1-(2-fluorophenyl)-2-(hydroxymethyl)-4-methoxycyclopentyl]amino}carbonothioyl)carbamateYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(1R*,2S*,4R*)-2-amino-2-(2-fluorophenyl)-4-methoxycyclopentyl]methanol (250 mg) and fluorenylmethyloxycarbonyl isothiocyanate (351 mg) in dichloromethane (20 mL) was stirred at room temperature for three days. The reaction solution was purified by silica gel column chromatography to obtain the title compound (340 mg).

Workup

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

Sources & evidence

ORD record
ord-7a598f8a2ed34c95abb114188a949898
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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