Diisopropylethylamine → HCID 58313057, compound

HRID 535122Notes

Reaction equation

HRID 535122 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:4][CH:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:40][O:41][C:42]([NH:44][C@H:45]([C:49](O)=[O:50])[CH:46]([CH3:48])[CH3:47])=[O:43].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:40][O:41][C:42]([NH:44][C@H:45]([C:49]([N:2]1[CH:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:1]1)=[O:50])[CH:46]([CH3:47])[CH3:48])=[O:43]

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 58313067HCID 58313067, compound

Product 1

HCID 58313057HCID 58313057, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 8-oxa-2-azaspiro[4.5]decane-3-carboxylate (101) (200 mg, 0.94 mmol), HATU (392 mg, 1.03 mmol) and N-[(methyloxy)carbonyl]-L-valine (181 mg, 1.03 mmol) in anhydrous CH2Cl2 (6 mL) was added Hunig's base (0.33 mL, 1.88 mmol) and the solution stirred at rt under nitrogen. After 2 h, the reaction was concentrated in vacuo, purified by C18 RP chromatography, eluting with 10-90% ACN/water/0.2% NH4OH, to afford the product as a yellow oil (313 mg, 90% yield).

Workup

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

Sources & evidence

ORD record
ord-d35be0d5d2d04e5c98ab39a8026fb613
Source dataset
uspto-grants-2014_10
Patent number
US08853416B2

Reaction notes

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