Diisopropylethylamine → 2-(1,1-dimethylethyl) 7-ethyl 6-{N-[(methyloxy)carbonyl]-L-valyl}-2,6-diazaspiro[3,4]octane-2,7-dicarboxylate

HRID 535138Notes

Reaction equation

HRID 535138 reaction equation
[CH2:1]1[C:4]2([CH2:8][CH:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][CH2:5]2)[CH2:3][N:2]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:45][O:46][C:47]([NH:49][C@H:50]([C:54](O)=[O:55])[CH:51]([CH3:53])[CH3:52])=[O:48].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:45][O:46][C:47]([NH:49][C@H:50]([C:54]([N:6]1[CH:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][C:4]2([CH2:3][N:2]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:1]2)[CH2:5]1)=[O:55])[CH:51]([CH3:52])[CH3:53])=[O:48]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10942966(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acidHCID 583130582-(Tert-butyl) 7-ethyl 2,6-diazaspiro[3.4]octane-2,7-dicarboxylate

Product 1

HCID 583130532-(1,1-dimethylethyl) 7-ethyl 6-{N-[(methyloxy)carbonyl]-L-valyl}-2,6-diazaspiro[3,4]octane-2,7-dicarboxylateYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1,1-dimethylethyl) 7-ethyl 2,6-diazaspiro[3.4]octane-2,7-dicarboxylate (145) (500 mg, 1.76 mmol), HATU (735 mg, 1.93 mmol) and N-[(methyloxy)carbonyl]-L-valine (339 mg, 1.93 mmol) in anhydrous CH2Cl2 (10 mL) was added Hunig's base (0.68 mL, 3.87 mmol) and the reaction stirred at room temperature under nitrogen for 2 h. The reaction was concentrated in vacuo and purified by C18 reverse-phase chromatography eluting with 10-90% ACN/water/0.2% NH4OH to afford the title compound as an off-white solid (398 mg, 51% yield).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by C18 reverse-phase chromatography
  3. washeluting with 10-90% ACN/water/0.2% NH4OH

Sources & evidence

ORD record
ord-fe65015f76ed451db88bc6a06216e58f
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

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