Dimethylformamide → HCID 68697903, compound

HRID 1876287Notes

Reaction equation

HRID 1876287 reaction equation
[CH3:1]CCP(=O)=O.[C:7]([O:11][C:12]([N:14]1[CH2:18][CH:17]2[CH2:19][CH2:20][CH2:21][CH:16]2[C@H:15]1[C:22]([OH:24])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].C([N:28]([CH:31]([CH3:33])C)[CH2:29][CH3:30])(C)C.[CH3:34][N:35](C=O)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH:17]2[CH2:19][CH2:20][CH2:21][CH:16]2[C@H:15]1[C:22](=[O:24])[NH:35][CH2:34][C:33]1[CH:31]=[N:28][CH:29]=[CH:30][CH:1]=1)=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 68699147HCID 68699147, compound

Product 1

HCID 68697903HCID 68697903, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

50% propylphosphonic anhydride solution in 650 μl of DMF is added to a solution of 200 mg of (S)-Hexahydro-cyclopenta[c]pyrrole-1,2-dicarboxylic acid 2-tert-butyl ester, 7.42 mg of 4-dimethylaminopyridine and 650 μl of diisopropylethylamine in CH2Cl2. After stirring at rt for 16 hours, the reaction is quenched with aq. 2N NaOH solution, eluted through a Chem Elut extraction with CH2Cl2 and solvent is evaporated before purification by preparative HPLC is carried out (Waters Sun Fire C18 column, gradient water/acetonitrile 95/5 to 0/100) to yield the title compound.

Workup

  1. customthe reaction is quenched with aq. 2N NaOH solution
  2. washeluted through a Chem Elut extraction with CH2Cl2 and solvent
  3. customis evaporated before purification by preparative HPLC

Sources & evidence

ORD record
ord-69b7c587599c4cdfa6512f053d7d73f6
Source dataset
uspto-grants-2012_11
Patent number
US08309596B2

Reaction notes

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