Triethylamine → HCID 45739920, compound

HRID 1170524Notes

Reaction equation

HRID 1170524 reaction equation
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH2:47]([NH2:57])[C:48]1[CH:56]=[CH:55][C:54]2[O:53][CH2:52][O:51][C:50]=2[CH:49]=1>CN(C=O)C.C(Cl)Cl>[C:12]([O:11][C:9]([N:1]1[CH2:8][CH2:7][CH2:6][CH:2]1[C:3](=[O:5])[NH:57][CH2:47][C:48]1[CH:56]=[CH:55][C:54]2[O:53][CH2:52][O:51][C:50]=2[CH:49]=1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 45739920HCID 45739920, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Boc-D-Pro-OH (209 mg, 0.970 mmol) was dissolved in DMF (4 mL), followed by addition of the HBTU (552 mg, 1.46 mmol) and Triethylamine (270 μL). The solution was stirred at room temperature for 30 minutes prior to the addition of piperonylamine (121 μL, 0.970 mmol). The reaction mixture stirred at rt for 16 h then the solution was transferred to a separatory funnel containing DCM (50 mL). The organic layer was washed with NaHCO3 (2×50 mL, sat. aq.) and dried over Na2SO4. The solution was concentrated and purified by prep LCMS to afford 278.0 mg (82.5%) of 2-[(benzo[1,3]dioxol-5-ylmethyl)-carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester. [M+H]+ 349.09.

Workup

  1. stirringThe reaction mixture stirred at rt for 16 h
  2. customthe solution was transferred to a separatory funnel
  3. washThe organic layer was washed with NaHCO3 (2×50 mL, sat. aq.)
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated
  6. custompurified by prep LCMS

Sources & evidence

ORD record
ord-b344dd2db00e4e54bb5f2f341e6142cd
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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