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

HRID 1036509Notes

Reaction equation

HRID 1036509 reaction equation
NC(C1C=CC2C(=CC=C(OC3C=CC(OC4C=CC=CC=4)=CC=3)C=2)C=1)(CO)CO.[CH2:31]([O:38][C:39]1[CH:64]=[CH:63][C:42]([O:43][C:44]2[CH:45]=[C:46]3[C:51](=[CH:52][CH:53]=2)[CH:50]=[C:49]([C:54]2([NH2:62])[CH2:59][O:58]C(C)(C)[O:56][CH2:55]2)[CH:48]=[CH:47]3)=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[NH2:62][C:54]([C:49]1[CH:48]=[CH:47][C:46]2[C:51](=[CH:52][CH:53]=[C:44]([O:43][C:42]3[CH:63]=[CH:64][C:39]([O:38][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:40][CH:41]=3)[CH:45]=2)[CH:50]=1)([CH2:55][OH:56])[CH2:59][OH:58]

Participants

3

Reactant 2

HCID 674236932-Amino-2-(6-(4-phenoxyphenoxy)naphthalen-2-yl)propane-1,3-diolHCID 674249415-(6-(4-(Benzyloxy)phenoxy)naphthalen-2-yl)-2,2-dimethyl-1,3-dioxan-5-amine

Product 1

HCID 674237562-Amino-2-(6-(4-(benzyloxy)phenoxy)naphthalen-2-yl)propane-1,3-diolYield 81%

Procedure

2-amino-2-(6-(4-(benzyloxy)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 81% yield using 5-(6-(4-(benzyloxy)phenoxy)naphthalen-2-yl)-2,2-dimethyl-1,3-dioxan-5-amine as starting material. MS: m/z=438.24 [M+Na+]. 1H NMR (MeOD) δ: 7.95 (s, 1H), 7.87 (d, J=9.0 Hz, 1H), 7.66-7.70 (m, 1H), 7.59-7.63 (m, 1H), 7.47 (d, J=7.5 Hz, 2H), 7.37-7.43 (m, 2H), 7.34 (d, J=7.0 Hz, 1H), 7.22 (dd, J=8.8, 2.5 Hz, 1H), 7.15 (d, J=2.3 Hz, 1H), 7.00-7.08 (m, 4H), 5.11 (s, 2H), 3.87-3.93 (m, 2H), 3.80-3.86 (m, 2H)

Sources & evidence

ORD record
ord-68d5e194eee943fc8debc49088203f86
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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