tert-butyl (S)-2-amino-3-cyclohexylpropylcarbamate → tert-butyl (2S)-3-cyclohexyl-2-(2-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)-3,4-dioxocyclobut-1-enylamino)propylcarbamate

HRID 1254227Notes

Reaction equation

HRID 1254227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:16](=[O:22])[C:17](=[O:21])[C:18]=2OC)[CH2:10]1.[NH2:29][C@@H:30]([CH2:40][CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36]>CC#N>[CH:41]1([CH2:40][C@H:30]([NH:29][C:18]2[C:17](=[O:21])[C:16](=[O:22])[C:15]=2[N:11]2[CH2:12][CH2:13][CH2:14][CH:9]([CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[O:23][CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH2:10]2)[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]1

Participants

4

Reactant 2

HCID 59382910tert-butyl (S)-2-amino-3-cyclohexylpropylcarbamateHCID 593830743-(3-((2-Fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)-4-methoxycyclobut-3-ene-1,2-dione

Product 1

HCID 57544930tert-butyl (2S)-3-cyclohexyl-2-(2-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)-3,4-dioxocyclobut-1-enylamino)propylcarbamateYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the crude 3-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)-4-methoxycyclobut-3-ene-1,2-dione in MeCN there was added tert-butyl (S)-2-amino-3-cyclohexylpropylcarbamate (27.0 mg, 0.11 mmol), the resulting solution was stirred at rt for 10 min, filtered through HPLC filter, purified by HPLC to give tert-butyl (2S)-3-cyclohexyl-2-(2-(3-((2-fluorophenyl)(3-methoxypropoxy)methyl)piperidin-1-yl)-3,4-dioxocyclobut-1-enylamino)propylcarbamate (17.4 mg, 40%) as on oil. MS ESI +ve m/z 616 (M+1).

Workup

  1. filtrationfiltered through HPLC
  2. filtrationfilter
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-9db3bd531f34403d9659f835161440eb
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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