Diisopropylethylamine → HCID 86670839, compound

HRID 709366Notes

Reaction equation

HRID 709366 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:10]([CH3:12])[CH3:11])[C:7]([OH:9])=O)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:37]1[C:41]2([CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[CH2:40][CH:39]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[NH:38]1.CCN(C(C)C)C(C)C>O.CN(C=O)C>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:10]([CH3:12])[CH3:11])[C:7]([N:38]1[C@H:39]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:40][C:41]2([CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[CH2:37]1)=[O:9])=[O:4]

Participants

7

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 58313067HCID 58313067, compound

Product 1

HCID 86670839HCID 86670839, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 50 ml round-bottomed flask, (S)-2-(methoxycarbonylamino)-3-methylbutanoic acid (813 mg, 4.64 mmol) was combined with DMF (10 ml) to give a colorless solution. HATU (1.76 g, 4.64 mmol) was added and stirred at room temperature for 10 min. Ethyl 8-oxa-2-azaspiro[4.5]decane-3-carboxylate (prepared according to the patent procedure described in WO 199808850) (900 mg, 4.22 mmol) and DIPEA (1.91 g, 2.58 ml, 14.8 mmol) were added and stirred overnight. It was diluted with H2O and extracted with EtOAc (2×100 ml). The organic layer was washed with brine and H2O, dried with MgSO4, filtered and concentrated in vacuo to afford (S)-ethyl 2-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-8-oxa-2-azaspiro[4.5]decane-3-carboxylate as a viscous oil (1.3 g, 83.2%). ESI-LRMS m/e calcd for C18H30N2O6 [M+] 370. found 371 [M+H+].

Workup

  1. customto give a colorless solution
  2. additionwere added
  3. stirringstirred overnight
  4. extractionextracted with EtOAc (2×100 ml)
  5. washThe organic layer was washed with brine and H2O
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af4c2e91aa5d43beae7edb83a4851f59
Source dataset
uspto-grants-2015_11
Patent number
US09180193B2

Reaction notes

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