tert-Butyl-5-(4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-ylsulfonyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → 4-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)-N-(3-methoxy-phenyl)-N-methyl benzenesulfonamide

HRID 710339Notes

Reaction equation

HRID 710339 reaction equation
C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](=[O:36])(=[O:35])[N:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=3)[CH3:26])=[CH:20][CH:19]=2)[CH2:13][O:12]C(C)(C)[O:10][CH2:9]1)(C)(C)C.C(OC(=O)NC1(CCC2C=CC(S(N3C4C(=CC=C(OC)C=4)C(C(=O)C4C=C(OC)C(OC)=C(OC)C=4)=C3)(=O)=O)=CC=2)COC(C)(C)OC1)(C)(C)C>>[NH2:7][C:8]([CH2:9][OH:10])([CH2:13][OH:12])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([N:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=2)[CH3:26])(=[O:35])=[O:36])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 131733939tert-Butyl-5-(4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-ylsulfonyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateHCID 131733943tert-Butyl-5-(4-(N-(3-methoxyphenyl)-N-methylsulfamoyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 580788074-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)-N-(3-methoxy-phenyl)-N-methyl benzenesulfonamideYield 80%

Procedure

When the product of Step D was substituted for tert-butyl-5-(4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-ylsulfonyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate in Example 13, Step F, the similar process afforded the title compound in 80% yield, as colourless solid. 1H-NMR (CDCl3) 1.87-1.93 (m, 2H); 2.65-2.71 (m, 2H); 3.05 (s, 3H); 3.62 (s, 3H); 3.70 (5, 4H); 6.55 (tr, 1H, J=2.20 Hz); 6.62 (d, 1H, J=7.62 Hz); 6.85 (dd, 1H, J=2.41, 8.34 Hz); 7.19 (tr, 1H, J=8.22 Hz); 7.34 (d, 2H, J=8.36 Hz); 7.43 (d, 2H, J=8.31 Hz).

Sources & evidence

ORD record
ord-892d49e041ca4b7dae8151bf281af359
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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