tert-Butyl-2,2-dimethyl-5-(2-(4'-methylbiphenyl-4-yl)ethyl)-1,3-dioxan-5-yl carbamate → 2-Amino-2-(2-(4'-methylbiphenyl-4-yl)ethyl)propane-1,3-diol

HRID 710341Notes

Reaction equation

C(=O)(O[C:4]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:9][O:8]C(C)(C)[O:6][CH:5]1C(C)(C)C)N.C(OC(=O)[NH:38]C1(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>>[NH2:38][C:4]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)([CH2:9][OH:8])[CH2:5][OH:6]

Participants

Reactant 2

HCID 66726778tert-Butyl-2,2-dimethyl-5-(2-(4'-methylbiphenyl-4-yl)ethyl)-1,3-dioxan-5-yl carbamate

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 461948902-Amino-2-(2-(4'-methylbiphenyl-4-yl)ethyl)propane-1,3-diolYield 67%

Procedure

When the product of Step A was substituted for tert-butyl-5-(4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-ylsulfonyl)-phenethyl)-2,2-di methyl-1,3-dioxan-5-ylcarbamate in Example 13, Step F, the similar process afforded the title compound in 67% yield, as colourless solid. 1H-NMR (CDCl3) 3.17-3.23 (m, 2H); 3.63 (s, 3H); 3.94-3.88 (m, 2H); 4.91 (d, 2H, J=12.36 Hz); 4.97 (d, 2H, J=11.94 Hz); 8.12 (tr, 4H, J=10.92 Hz); 8.66-8.88 (m, 4H).

Sources & evidence

ORD record: ord-5f2638cf77164b4c9002b9340fd1a964
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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