N-{[(3S,4R,6R)-6-[(benzyloxy)methyl]-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide → rel-N-({(3S,4R,6R)-6-cyclopropyl-3-(2,4-difluorophenyl)-4-[(1R)-1-hydroxy-2-methoxyethyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide

HRID 1478735Notes

Reaction equation

HRID 1478735 reaction equation
[NH2:1][C@@:2]1([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH2:7][O:6][C@@H:5]([CH:8]2[CH2:10][CH2:9]2)[CH2:4][C@H:3]1[C@@H:11]([OH:15])[CH2:12][O:13][CH3:14].C(OC[C@@H]1OC[C@@](N[C:48]([NH:50][C:51](=[O:58])[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[S:49])(C2C=CC(F)=CC=2F)[C@H](CO)C1)C1C=CC=CC=1>>[CH:8]1([C@@H:5]2[O:6][CH2:7][C@@:2]([NH:1][C:48]([NH:50][C:51](=[O:58])[C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)=[S:49])([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[F:23])[C@H:3]([C@@H:11]([OH:15])[CH2:12][O:13][CH3:14])[CH2:4]2)[CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 86701080N-{[(3S,4R,6R)-6-[(benzyloxy)methyl]-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamideHCID 90253562rel-(1R)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]-2-methoxyethanol

Product 1

HCID 90253553rel-N-({(3S,4R,6R)-6-cyclopropyl-3-(2,4-difluorophenyl)-4-[(1R)-1-hydroxy-2-methoxyethyl]tetrahydro-2H-pyran-3-yl}carbamothioyl)benzamide

Procedure

Conversion of rel-(1R)-1-[(2R,4R,5S)-5-amino-2-cyclopropyl-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]-2-methoxyethanol (C40) to the product was carried out via the method described for synthesis of N-{[(3S,4R,6R)-6-[(benzyloxy)methyl]-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide (C7) in Preparation P1. In this case, purification was effected via silica gel chromatography (Gradient: 0% to 60% ethyl acetate in heptane), affording the product as a solid. Yield: 0.55 g, 1.1 mmol, 43%.

Workup

  1. customIn this case, purification

Sources & evidence

ORD record
ord-d3e2dd7e11164e94a3d00303625316e8
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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