[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol → 9H-fluoren-9-ylmethyl {[(3S,4R,6R)-6-[(benzyloxy)methyl]-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}carbamate

HRID 1427399Notes

Reaction equation

HRID 1427399 reaction equation
[NH2:1][C@@:2]1([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[CH2:7][O:6][C@@H:5]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][C@H:3]1[CH2:17][OH:18].FC1C=C(F)C=CC=1[C@@]1(N[C:44]([NH:46][C:47](=[O:63])[O:48][CH2:49][CH:50]2[C:62]3[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=3[C:56]3[C:51]2=[CH:52][CH:53]=[CH:54][CH:55]=3)=[S:45])[C@H](CO)CCOC1>>[CH2:10]([O:9][CH2:8][C@@H:5]1[O:6][CH2:7][C@@:2]([NH:1][C:44]([NH:46][C:47](=[O:63])[O:48][CH2:49][CH:50]2[C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][C:56]=3[C:57]3[C:62]2=[CH:61][CH:60]=[CH:59][CH:58]=3)=[S:45])([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[C@H:3]([CH2:17][OH:18])[CH2:4]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 71277793[(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanolHCID 866771049H-fluoren-9-ylmethyl {[(3S,4R)-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}carbamate

Product 1

HCID 866771069H-fluoren-9-ylmethyl {[(3S,4R,6R)-6-[(benzyloxy)methyl]-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}carbamate

Procedure

Conversion of [(2R,4R,5S)-5-amino-2-[(benzyloxy)methyl]-5-(2,4-difluorophenyl)tetrahydro-2H-pyran-4-yl]methanol (C22) to the product was carried out according to the general procedure for the synthesis of 9H-fluoren-9-ylmethyl {[(3S,4R)-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}carbamate (C12) in Example 1. The product was obtained as a white solid. Yield: 995 mg, 1.54 mmol, 75%. LCMS m/z 645.6 (M+1). 1H NMR (400 MHz, CDCl3), characteristic peaks: δ 3.52 (dd, J=10.3, 4.1 Hz, 1H), 3.64 (dd, J=10.2, 6.0 Hz, 1H), 4.46 (dd, half of ABX pattern, J=10.6, 6.9 Hz, 1H), 4.60 (AB quartet, JAB=12.0 Hz, ΔνAB=11.1 Hz, 2H), 6.73-6.81 (m, 1H), 6.86-6.92 (m, 1H), 7.20-7.25 (m, 1H), 7.42-7.48 (m, 2H), 7.54-7.59 (m, 2H).

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-4329fa81e0914909a2ae70f69657ea67
Source dataset
uspto-grants-2015_01
Patent number
US08933221B2

Reaction notes

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