2-Amino-2-(6-(4-phenoxyphenoxy)naphthalen-2-yl)propane-1,3-diol → 2-Amino-2-(6-(4-(pentyloxy)phenoxy)naphthalen-2-yl)propane-1,3-diol

HRID 2389172Notes

Reaction equation

HRID 2389172 reaction equation
[NH2:1][C:2]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4C=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[CH:13]=2)[CH:8]=1)([CH2:5][OH:6])[CH2:3][OH:4].CC1(C)OCC(C2C=CC3C(=CC=C(OC4C=CC(OCCCCC)=CC=4)C=3)C=2)(N)CO1>>[NH2:1][C:2]([C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:20][CH:19]=3)[CH:13]=2)[CH:8]=1)([CH2:3][OH:4])[CH2:5][OH:6]

Participants

3

Reactant 2

HCID 674236932-Amino-2-(6-(4-phenoxyphenoxy)naphthalen-2-yl)propane-1,3-diolHCID 674254772,2-Dimethyl-5-(6-(4-(pentyloxy)phenoxy)naphthalen-2-yl)-1,3-dioxan-5-amine

Product 1

HCID 674131492-Amino-2-(6-(4-(pentyloxy)phenoxy)naphthalen-2-yl)propane-1,3-diolYield 55%

Procedure

2-amino-2-(6-(4-(pentyloxy)phenoxy)naphthalen-2-yl)propane-1,3-diol was synthesized as per 2-amino-2-(6-(4-phenoxyphenoxy)naphthalen-2-yl)propane-1,3-diol (Example 245) in 55% yield using 2,2-dimethyl-5-(6-(4-(pentyloxy)phenoxy)naphthalen-2-yl)-1,3-dioxan-5-amine as starting material. MS: m/z=418.45 [M+Na+]. 1H NMR (MeOD) δ: 7.88-7.94 (m, 2H), 7.78 (d, J=8.8 Hz, 1H), 7.51 (dd, J=8.8, 2.0 Hz, 1H), 7.30 (dd, J=9.0, 2.5 Hz, 1H), 7.17 (d, J=2.3 Hz, 1H), 7.01-7.07 (m, 2H), 6.94-7.01 (m, 2H), 4.05-4.12 (m, 2H), 3.96-4.02 (m, 4H), 1.70-1.85 (m, 2H), 1.37-1.54 (m, 4H), 0.92-1.01 (m, 3H)

Sources & evidence

ORD record
ord-5cdf8f8546644f4a9c478bf94a6b59d9
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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