tert-Butyl 5-(4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfamoyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → 4-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)-N-(6,6-dimethyl-bicyclo[3.1.1]heptan-2-yl)benzenesulfonamide

HRID 710344Notes

Reaction equation

[CH3:1][C:2]1([CH3:37])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[NH:9][S:10]([C:13]1[CH:36]=[CH:35][C:16]([CH2:17][CH2:18][C:19]2([NH:27]C(=O)OC(C)(C)C)[CH2:24][O:23]C(C)(C)[O:21][CH2:20]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11].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>>[NH2:27][C:19]([CH2:20][OH:21])([CH2:24][OH:23])[CH2:18][CH2:17][C:16]1[CH:35]=[CH:36][C:13]([S:10]([NH:9][CH:6]2[CH2:5][CH2:4][CH:3]3[CH2:8][CH:7]2[C:2]3([CH3:37])[CH3:1])(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 86661778tert-Butyl 5-(4-(N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)sulfamoyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

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

Product 1

HCID 667265364-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)-N-(6,6-dimethyl-bicyclo[3.1.1]heptan-2-yl)benzenesulfonamideYield 80%

Procedure

When the product of Step C 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 (D2O) 0.67 (s, 3H); 0.94 (s, 3H); 1.14-1.17 (m, 2H); 1.71 (m, 6H); 1.88-2.01 (b, 4H); 2.17 (m, 1H); 2.67-2.78 (m, 4H); 3.68 (s, 4H); 7.42 (d, 2H, J=8.17 Hz); 7.70 (d, 2H, J=8.18 Hz).

Sources & evidence

ORD record: ord-8ad0653ceca04c939bd1f2dafc26c3b8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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