Triethylamine → HCID 90449553, compound

HRID 1411316Notes

Reaction equation

HRID 1411316 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]2([C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH:22]4[CH2:25][CH:24]([C:26]([OH:28])=O)[CH2:23]4)[CH:19]=3)[N:14]([C:29]([O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])=[O:30])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH:39]1[CH2:42][CH2:41][CH2:40]1.C(N(CC)CC)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[N:39]1([C:26]([CH:24]2[CH2:23][CH:22]([CH2:21][C:18]3[CH:19]=[C:20]4[C:10]5([CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9]5)[CH2:13][N:14]([C:29]([O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])=[O:30])[C:15]4=[CH:16][CH:17]=3)[CH2:25]2)=[O:28])[CH2:42][CH2:41][CH2:40]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 12308726Azetidine hydrochlorideHCID 90449461HCID 90449461, compound

Product 1

HCID 90449553HCID 90449553, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-((1′-(tert-Butoxycarbonyl)-1-((2-(trimethylsilyl)ethoxy)carbonyl)spiro[indoline-3,3′-pyrrolidin]-5-yl)methyl)cyclobutanecarboxylic acid (17.5 mg, 0.033 mmol) was dissolved in methylene chloride (1 mL) Thereafter, azetidine hydrochloride (6.0 mg, 0.064 mmol), triethylamine (9.0 μL, 0.065 mmol), and PyBOP (34.0 mg, 0.065 mmol) were added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred for 15 hours. Thereafter, water was added to the reaction solution, and the mixed solution was then extracted with chloroform. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-((3-(azetidine-1-carbonyl)cyclobutyl)methyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (11.2 mg, 60%) in the form of a light brown oily product.

Workup

  1. extractionthe mixed solution was then extracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. concentrationfollowed by concentration in vacuo
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-ddfd1b3cb7a245e092d4522c9cf257c5
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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