tert-Butyl-5-(4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-ylsulfonyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → 2-Amino-2-(3-(3,4,5-trimethoxyphenethyl)phenethyl)propane-1,3-diol

HRID 710349Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][C:26]3[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=3)[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]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][C:26]2[CH:27]=[C:28]([O:36][CH3:37])[C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=2)[CH:19]=1)([CH2:13][OH:12])[CH2:9][OH:10]

Participants

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-ylcarbamate

HCID 131733949tert-Butyl-2,2-dimethyl-5-(3-(3,4,5-trimethoxyphenethyl)phenethyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461948872-Amino-2-(3-(3,4,5-trimethoxyphenethyl)phenethyl)propane-1,3-diolYield 74%

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 74% yield, as colourless solid. 1H-NMR (CDCl3) 1.7-1.8 (m, 2H); 2.51-2.52 (m, 2H); 2.77 (s, 4H); 3.31-3.42 (m, 13H); 6.26 (s, 2H); 6.81 (s, 1H); 6.95-6.97 (m, 2H); 7.13 (tr, 1H, J=7.44 Hz).

Sources & evidence

ORD record: ord-42541fae69074ff4a2cfc53174bf4271
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

Loading…