tert-Butyl-2,2-dimethyl-5-(4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)propyl)phenethyl)-1,3-dioxan-5-ylcarbamate → (1-(4-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)phenylsulfonyl)-6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 710327Notes

Reaction equation

HRID 710327 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]([N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=4)[C:29]([C:38](=[O:51])[C:39]4[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][CH3:48])=[C:41]([O:49][CH3:50])[CH:40]=4)=[CH:28]3)(=[O:26])=[O:25])=[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(CCCN3C4C(=CC=CC=4)C(C(=O)C(F)(F)F)=C3)=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:19]=[CH:20][C:21]([S:24]([N:27]2[C:35]3[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=3)[C:29]([C:38]([C:39]3[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][CH3:48])=[C:41]([O:49][CH3:50])[CH:40]=3)=[O:51])=[CH:28]2)(=[O:25])=[O:26])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 131733935tert-Butyl-2,2-dimethyl-5-(4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)propyl)phenethyl)-1,3-dioxan-5-ylcarbamateHCID 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 46195025(1-(4-(3-Amino-4-hydroxy-3-(hydroxymethyl)butyl)phenylsulfonyl)-6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanoneYield 65%

Procedure

When the product of Step E was substituted for tert-butyl-2,2-dimethyl-5-(4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)propyl)phenethyl)-1,3-dioxan-5-ylcarbamate in Example 11, Step F, the identical process afforded the title compound in 65% yield, as colourless solid. 1H-NMR (D2O) 1.65-1.68 (m, 2H); 2.44-2.46 (m, 2H); 3.50 (s, 3H); 3.56 (s, 3H); 3.59 (s, 6H), 6.10 (d, 1H, J=8.77 Hz); 6.55 (broad s, 2H); 6.98 (s, 2H); 7.18-7.20 (m, 2H); 7.60-7.62 (m, 3H).

Sources & evidence

ORD record
ord-baecbfb258d4492385c7100da142ce0d
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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