Dichloromethane → HCID 178512563, compound

HRID 1441381Notes

Reaction equation

HRID 1441381 reaction equation
C(OC([NH:8]/[C:9](/[NH:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:35][CH2:34][CH2:33][C@@H:26]2[C:27]([NH:29][CH:30]2[CH2:32][CH2:31]2)=[O:28])=[CH:21][CH:20]=1)=[N:10]/C(OC(C)(C)C)=O)=O)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>CO>[CH:30]1([NH:29][C:27]([C@H:26]2[CH2:33][CH2:34][CH2:35][N:25]2[C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:9]([NH2:10])=[NH:8])=[CH:24][CH:23]=2)=[O:28])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 6422Trifluoroacetic acidHCID 178454299HCID 178454299, compound

Product 1

HCID 178512563HCID 178512563, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 1-[4-({(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)phenyl]-N-cyclopropyl-D-prolinamide (Method 62; 2.0 g) was added DCM (60 ml) and TFA (20 ml). The reaction stirred for 4 hours before removal of the solvent in vacuo. To the gum was added DCM (75 ml) and macroporous polystyrene carbonate resin (0.49 g of capacity 3.0 m.equ per g) solid supported reagent (20 g), the reaction was slowly stirred overnight. The reaction was filtered and the solvent removed in vacuo to yield very little product. A white solid was present in the filter cup, this was dissolved in MeOH, the resin was also added to the MeOH, the system was stirred for 10 minutes before being filtered, the solvent was removed in vacuo to yield the title compound as a white solid (0.90 g, 75%). NMR (299.954 MHz, CDCl3) δ 7.26 (s, 3H), 6.85 (d, 2H), 6.49 (d, 2H), 3.93 (d, 1H), 3.62-3.60 (m, 1H), 3.17 (q, 1H), 2.70-2.62 (m, 1H), 2.32-2.14 (m, 2H), 2.00-1.92 (m, 2H), 0.76-0.63 (m, 2H), 0.42 (q, 2H); m/z 287.

Workup

  1. waitthe reaction was slowly stirred overnight
  2. filtrationThe reaction was filtered
  3. customthe solvent removed in vacuo
  4. customto yield very little product
  5. stirringthe system was stirred for 10 minutes
  6. filtrationbefore being filtered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d7dd1b212fc34a40963091af7b8b7128
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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