Fmoc isothiocyanate → 9H-fluoren-9-ylmethyl {[(3S,4R)-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}carbamate

HRID 1427391Notes

Reaction equation

HRID 1427391 reaction equation
[C:1]([N:18]=[C:19]=[S:20])(=[O:17])[O:2][CH2:3][CH:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.[NH2:21][C@:22]1([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=2[F:37])[C@H:27]([CH2:28][OH:29])[CH2:26][CH2:25][O:24][CH2:23]1>ClCCl>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[C@@:22]1([NH:21][C:19]([NH:18][C:1](=[O:17])[O:2][CH2:3][CH:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C:11]3[C:16]2=[CH:15][CH:14]=[CH:13][CH:12]=3)=[S:20])[C@H:27]([CH2:28][OH:29])[CH2:26][CH2:25][O:24][CH2:23]1

Participants

4

Reactant 2

HCID 4154759Fmoc isothiocyanateHCID 71277791[(3S,4R)-3-amino-3-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol

Product 1

HCID 866771049H-fluoren-9-ylmethyl {[(3S,4R)-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9H-Fluoren-9-ylmethyl carbonisothiocyanatidate (Fmoc-isothiocyanate) (827 mg, 2.94 mmol) was added to a solution of [(3S,4R)-3-amino-3-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol (C11) (650 mg, 2.67 mmol) in dichloromethane (10 mL), and the reaction mixture was allowed to stir for 4 hours at room temperature. Removal of solvent in vacuo provided a paste, which was purified via silica gel chromatography (Gradient: 0% to 5% methanol in dichloromethane) to afford the product. Yield: 1.17 g, 2.23 mmol, 84%. LCMS m/z 525.2 (M+1).

Workup

  1. customRemoval of solvent in vacuo
  2. customprovided a paste, which
  3. customwas purified via silica gel chromatography (Gradient: 0% to 5% methanol in dichloromethane)
  4. customto afford the product

Sources & evidence

ORD record
ord-50d1348f0b924cd28478183e10c5696d
Source dataset
uspto-grants-2015_01
Patent number
US08933221B2

Reaction notes

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