Hydrochloric Acid → HCID 67413125, compound

HRID 2273051Notes

Reaction equation

HRID 2273051 reaction equation
N1(C(NC(=O)OC(C)(C)C)NC(=O)[O-])C=CC=N1.[O:19]=[C:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:33])OC(C)(C)C)[CH2:22][CH2:21]1.Cl.[N:35]1([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:42][CH2:41][CH2:40][C@H:36]1C(O)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[O:19]=[C:20]1[CH2:21][CH2:22][CH:23]([NH:26][C:27]([C@@H:36]2[CH2:40][CH2:41][CH2:42][N:35]2[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[O:33])[CH2:24][CH2:25]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86635872HCID 86635872, compound

Product 1

HCID 67413125HCID 67413125, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To prepare compound 2 of Scheme 7-1, tert-Butyl 4-oxocyclohexylcarbamate (9.0 g, 42.5 mmol) was treated with HCl (4N in 1,4-dioxane, 60 mL) at rt. After 4 h stirring, the reaction was concentrated to obtain the crude product (6.3 g), which was dissolved in anhydrous DMF (200 mL). N-Boc-L-Pro-OH (9.1 g, 42.3 mmol)), HATU (17.7 g, 46.6 mmol) and DIEA (22.8 mL, 131 mmol) were added at rt. After stirring overnight, the reaction was quenched by brine, extracted by ethyl acetate. The combined organic phases were washed with brine and H2O, dried with Na2SO4. After removal of the solvents, the crude product was purified by silica gel column chromatography (ethyl acetate) to afford (S)-tert-butyl 2-(4-oxocyclohexylcarbamoyl)pyrrolidine-1-carboxylate (7.5 g, 57% yield).

Workup

  1. concentrationthe reaction was concentrated
  2. customto obtain the crude product (6.3 g), which
  3. stirringAfter stirring overnight
  4. customthe reaction was quenched by brine
  5. extractionextracted by ethyl acetate
  6. washThe combined organic phases were washed with brine and H2O
  7. dry with materialdried with Na2SO4
  8. customAfter removal of the solvents
  9. customthe crude product was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-8577e0db00cf4559b7b6e45a9cac4501
Source dataset
uspto-grants-2015_09
Patent number
US09120779B2

Reaction notes

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