HCID 29945350, compound → HCID 57060952, compound

HRID 1815558Notes

Reaction equation

HRID 1815558 reaction equation
[NH2:1][C@@H:2]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)[C@H:3]([OH:22])[CH2:4][N:5]([CH2:18][CH:19]([CH3:21])[CH3:20])[S:6]([C:9]1[CH:17]=[CH:16][C:12]2[O:13][CH2:14][O:15][C:11]=2[CH:10]=1)(=[O:8])=[O:7].[C:38](=O)([O:49]C1C=CC([N+]([O-])=O)=CC=1)[O:39][CH:40]1[CH:48]2[CH:43]([O:44][CH2:45][CH2:46][CH2:47]2)[O:42][CH2:41]1.C(N(C(C)C)CC)(C)C.C(#N)C>ClCCl.CO>[O:13]1[C:12]2[CH:16]=[CH:17][C:9]([S:6]([N:5]([CH2:18][CH:19]([CH3:20])[CH3:21])[CH2:4][C@@H:3]([OH:22])[C@@H:2]([NH:1][C:38](=[O:49])[O:39][CH:40]3[CH:48]4[CH:43]([O:44][CH2:45][CH2:46][CH2:47]4)[O:42][CH2:41]3)[CH2:23][C:24]3[CH:25]=[CH:26][C:27]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:28][CH:29]=3)(=[O:7])=[O:8])=[CH:10][C:11]=2[O:15][CH2:14]1

Participants

4

Reactant 2

HCID 29945350HCID 29945350, compoundHCID 86593031HCID 86593031, compound

Product 1

HCID 57060952HCID 57060952, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

N{(2R,3S)-3-Amino-4-[4-(benzyloxy)phenyl]-2-hydroxybutyl}-N-isobutyl-1,3-benzodioxole-5-sulfonamide was treated with hexahydro-4H-furo[2,3-b]pyran-3-yl 4-nitrophenyl carbonate/diisopropylethylamine/acetonitrile as previously described to afford after silica gel chromatography (dichloromethane/methanol 49:1) the title diastereomers as a solid foams. Diastereomer A: 1H NMR (DMSO-d6): δ 0.76 (3H, d), 0.80 (3H, d), 1.2 (1H, br s), 1.6 (2H, br s), 1.9 (1H, br s), 2.1 (1H, br s), 2.4 (1H, br s), 2.75 (1H, dd), 2.8-3.0 (3H, m), 3.2-3.3 (3H, m), 3.4-3.6 (3H, m), 3.7 (1H, d), 4.0 (1H, t), 4.8-4.9 (2H, m), 5.0 (3H, br s), 6.15 (2H, s), 6.8 (2H, d), 7.0-7.2 (4H, m), 7.21-7.42 (7H, m); MS: 719 (M+23) Diastereomer B: 1H NMR (DMSO-d6): δ 0.76 (3H, d), 0.82 (3H, d), 1.0 (1H, br s), 1.3 (1H, br s), 1.5 (1H, br s), 1.95 (2H, br s), 2.4 (1H, t), 2.7 (2H, td), 2.9 (1H, d), 2.97 (1H, dd), 3.2-3.3 (3H, m), 3.5 (1H, br s), 3.55 (1H, br s), 3.64 (2H, br s), 4.0 (1H, dd), 4.9 (1H, s), 4.95-5.05 (4H, m), 6.15 (2H, s), 6.8 (2H, d), 7.0-7.2 (4H, m), 7.22 (1H, s), 7.25-7.40 (6H, m); MS: 719 (M+23)

Sources & evidence

ORD record
ord-3f86420c99e64f168ee3fffb2f87be74
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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