3-(Benzyloxy)benzene-1-thiol → 2-Amino-2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)propane-1,3-diol

HRID 2389124Notes

Reaction equation

HRID 2389124 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:26]C(=O)OC(C)(C)C)([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=3)[CH:9]=2)[CH2:4][O:3]1.[CH2:35]([O:42][C:43]1[CH:44]=[C:45]([SH:49])[CH:46]=[CH:47][CH:48]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[NH2:26][C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:49][C:45]3[CH:46]=[CH:47][CH:48]=[C:43]([O:42][CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:44]=3)[CH:14]=2)[CH:9]=1)([CH2:4][OH:3])[CH2:6][OH:7]

Participants

3

Reactant 2

HCID 249006013-(Benzyloxy)benzene-1-thiolHCID 86642898Tert-butyl 2,2-dimethyl-5-(6-(trifluoromethylsulfonyloxy)naphthalen2-yl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461963582-Amino-2-(6-(3-(benzyloxy)phenylthio)naphthalen-2-yl)propane-1,3-diol

Procedure

The compound was prepared from tert-butyl 2,2-dimethyl-5-(6-(trifluoromethylsulfonyloxy)naphthalen2-yl)-1,3-dioxan-5-ylcarbamate and 3-benzyloxy-benzenethiol in reactions analogous to those described in Examples 154 and 191. 1H NMR (MeOD) δ: 7.82 (s, 1H), 7.76 (d, J=8.6 Hz, 2H), 7.71 (s, 1H), 7.48 (dd, J=8.6, 2.0 Hz, 1H), 7.31 (dd, J=8.6, 1.5 Hz, 1H), 7.11-7.26 (m, 6H), 6.80-6.89 (m, 3H), 4.93 (s, 2H), 3.95-4.03 (m, 2H), 3.86-3.94 (m, 2H). MS (M+1): 432.0.

Sources & evidence

ORD record
ord-1885be9da17246ba834392b577532e64
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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