pivalic acid (S)-6-(2-ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester → (S)-6-{2-{[4-(2-Amino-2-methylpropoxy)benzyl]ethylamino}phenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950248Notes

Reaction equation

HRID 1950248 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C@H:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([O:20]C(=O)C(C)(C)C)[CH:14]=[CH:13][C:12]=2[CH2:11]1)[CH3:2].C(OC(=O)[NH:33][C:34]([CH3:46])([CH3:45])[CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]=O)=[CH:39][CH:38]=1)(C)(C)C>>[NH2:33][C:34]([CH3:45])([CH3:46])[CH2:35][O:36][C:37]1[CH:38]=[CH:39][C:40]([CH2:43][CH2:2][CH2:1][NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C@H:10]2[CH2:19][CH2:18][C:17]3[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13][C:12]=3[CH2:11]2)=[CH:41][CH:42]=1

Participants

3

Reactant 2

HCID 57934051pivalic acid (S)-6-(2-ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 57934200Tert-butyl[2-(4-formylphenoxy)-1,1-dimethylethyl]carbamate

Product 1

HCID 66626236(S)-6-{2-{[4-(2-Amino-2-methylpropoxy)benzyl]ethylamino}phenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 52.7%

Procedure

Synthesized from pivalic acid (S)-6-(2-ethylaminophenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) and tert-butyl[2-(4-formylphenoxy)-1,1-dimethylethyl]carbamate (125 mg) according to an analogous synthetic method to Example 238 and purified by LC-MS, the title compound (20 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-eea5e473c09848f8a89514b96a67a838
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

Loading…