Ammonia → Pivalic acid 6-{2-{[4-(2-amino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

HRID 1950183Notes

Reaction equation

HRID 1950183 reaction equation
C(OC([NH:8][C:9]([CH3:48])([CH3:47])[CH2:10][O:11][C:12]1[CH:46]=[CH:45][C:15]([CH2:16][CH2:17][CH2:18][NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[CH:28]2[CH2:37][CH2:36][C:35]3[CH:34]=[C:33]([O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[CH:32]=[CH:31][C:30]=3[CH2:29]2)=[CH:14][CH:13]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.O1CCCC1.N>ClCCl>[NH2:8][C:9]([CH3:48])([CH3:47])[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH2:17][CH2:18][NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=2[CH:28]2[CH2:37][CH2:36][C:35]3[CH:34]=[C:33]([O:38][C:39](=[O:44])[C:40]([CH3:41])([CH3:42])[CH3:43])[CH:32]=[CH:31][C:30]=3[CH2:29]2)=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 66627582Pivalic acid 6-{2-{[4-(2-tert-butoxycarbonylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 66627097Pivalic acid 6-{2-{[4-(2-amino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl esterYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of pivalic acid 6-{2-{[4-(2-tert-butoxycarbonylamino-2-methylpropoxy)benzyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (90 mg) in dichloromethane (1.5 ml) was added trifluoroacetic acid (0.2 ml), and the solution was stirred for 1.5 hours at room temperature. The solution was neutralized by sequentially adding tetrahydrofuran and aqueous ammonia, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (72 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washsequentially washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-5dbdbdf5d8194ffba1180bc4789adda2
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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