تفاعل #2069938

ord-03c59ebf47294017877d142b189c3983

معادلة التفاعل

CCOC(=O)n1nc(N)c2c1CN(C(=O)OC(C)(C)C)C2
3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester
CCN(C(C)C)C(C)C
DIEA
O=C(Cl)C(=O)Cl
(COCl)2
CC(C(=O)O)c1ccc2ccccc2c1
2-naphthalen-2-yl-propionic acid
CCOC(=O)n1nc(NC(=O)C(C)c2ccc3ccccc3c2)c2c1CN(C(=O)OC(C)(C)C)C2
title compound
المردود 93.0%
CCOC(=O)n1nc(NC(=O)C(C)c2ccc3ccccc3c2)c2c1CN(C(=O)OC(C)(C)C)C2
3-(2-Naphthalen-2-yl-propionylamino)-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester
المردود 93.0%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    تركيزThe reaction mixture was concentrated under vacuum
  2. 2
    تركيزconcentrated
  3. 3
    أخرىto reach r.t.
  4. 4
    workup.STIRRINGstirred overnight
  5. 5
    ترشيحThe mixture was filtered
  6. 6
    أخرىthe solution evaporated to dryness under vacuum
  7. 7
    workup.DISSOLUTIONThe resulting residue was dissolved in DCM
  8. 8
    غسيلthe obtained solution was washed with brine
  9. 9
    تجفيفdried over sodium sulfate
  10. 10
    ترشيحfiltered
  11. 11
    أخرىevaporated to dryness
  12. 12
    أخرىThe crude product was purified by flash-chromatography (eluent

الإجراء التجريبي

To a solution of 2-naphthalen-2-yl-propionic acid (1.48 g. 7.4 mmol) in DCM (40 ml) and DMF cat., (COCl)2 (0.83 ml, 9.65 mmol) in DCM (10 ml) was added dropwise. The mixture was stirred at r.t. for 30 min. The reaction mixture was concentrated under vacuum, reconstituted twice with toluene and concentrated. A solution of the obtained acyl-chloride in THF (40 ml) was added slowly to a mixture of 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester (2.0 g, 6.75 mmol) and DIEA (5.8 ml, 33.3 mmol) in THF (40 ml) at 0-5° C. The reaction was allowed to reach r.t. and stirred overnight. The mixture was filtered and the solution evaporated to dryness under vacuum. The resulting residue was dissolved in DCM and the obtained solution was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash-chromatography (eluent:ethyl acetate/cyclohexane 3/7 then 4/6) to give 3.0 g (93% yield) of the title compound as a white solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07541354B2uspto-grants-2009_06