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-(3-1-admantanyl-4-isopropoxyphenethyl)propane-1,3-diol

HRID 710362Notes

Reaction equation

HRID 710362 reaction equation
C(OC(=O)[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([C:28]34[CH2:37][CH:32]5[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]5)[CH2:29]3)[CH2:35]4)[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][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([C:28]23[CH2:37][CH:32]4[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]4)[CH2:29]2)[CH2:35]3)[CH:19]=1)([CH2:13][OH:12])[CH2:9][OH:10]

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 131733956tert-Butyl-5-(3-1-admantanyl-4-isopropoxyphenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461951722-Amino-2-(3-1-admantanyl-4-isopropoxyphenethyl)propane-1,3-diolYield 67%

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 67% yield, as a creamy paste. 1H-NMR (CDCl3) 1.28 (d, 6H, J=6 Hz); 1.68 (s, 6H); 1.82-1.88 (m, 2H); 1.97 (s, 3H); 2.02 (s, 6H); 2.47-2.54 (m, 2H); 3.61 (d, 2H, J=12.1 Hz); 3.68 (d, 2H, J=12.1 Hz); 4.48-4.57 (m, 1H); 6.68 (d, 1H, J=8.4 Hz); 6.88 (dd, 1H, J=8.29, 2.1 Hz); 6.94 (d, 1H, J=2.14 Hz).

Sources & evidence

ORD record
ord-04ca7b94d9f54c18b407f7babbf1ec50
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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