Dicyclohexylcarbodiimide → HCID 71046453, compound

HRID 2374801Notes

Reaction equation

HRID 2374801 reaction equation
O[N:2]1C(=O)[CH2:5][CH2:4][C:3]1=[O:8].C1([N:15]=C=NC2CCCCC2)CCCCC1.C(O[C:29]([C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[S:36]([C:39]1[N:43]2[C@:44]([CH3:69])([CH2:56][C:57]3[CH:62]=[CH:61][C:60]([C:63]4[CH:64]=[N:65][CH:66]=[N:67][CH:68]=4)=[CH:59][CH:58]=3)[C:45](=[O:55])[N:46]([C:47]3[CH:52]=[C:51]([Cl:53])[CH:50]=[C:49]([Cl:54])[CH:48]=3)[C:42]2=[N:41][CH:40]=1)(=[O:38])=[O:37])=[O:30])(C)(C)C>C(Cl)Cl>[C:3]([C@H:4]([NH:15][C:29]([C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[S:36]([C:39]1[N:43]2[C@:44]([CH3:69])([CH2:56][C:57]3[CH:62]=[CH:61][C:60]([C:63]4[CH:64]=[N:65][CH:66]=[N:67][CH:68]=4)=[CH:59][CH:58]=3)[C:45](=[O:55])[N:46]([C:47]3[CH:52]=[C:51]([Cl:53])[CH:50]=[C:49]([Cl:54])[CH:48]=3)[C:42]2=[N:41][CH:40]=1)(=[O:38])=[O:37])=[O:30])[CH3:5])(=[O:8])[NH2:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 12136449(S)-1-[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-pyrimidin-5-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

Product 1

HCID 71046453HCID 71046453, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Hydroxysuccinimide (0.035 g), followed by 1,3-dicyclohexylcarbodiimide (DCC, 0.064 g), were added to a solution of (S)-1-[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-pyrimidin-5-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid (Example 14) (0.16 g) in CH2Cl2 (20 mL). The reaction was stirred at room temperature for 1 h, then was filtered through a pad of diatomaceous earth, concentrated and re-dissolved in 2N NH3—CH3OH (10 mL). The solution was stirred at room temperature for 1 h. The volatiles were then removed and the resultant residue was re-dissolved in CH2Cl2 and washed with H2O. The combined organic layers were concentrated and the resultant residue was purified by silica gel chromatography to afford the title compound (0.128 g) as a foam (697.2, M+1).

Workup

  1. filtrationwas filtered through a pad of diatomaceous earth
  2. concentrationconcentrated
  3. dissolutionre-dissolved in 2N NH3—CH3OH (10 mL)
  4. stirringThe solution was stirred at room temperature for 1 h
  5. customThe volatiles were then removed
  6. dissolutionthe resultant residue was re-dissolved in CH2Cl2
  7. washwashed with H2O
  8. concentrationThe combined organic layers were concentrated
  9. customthe resultant residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0e2990a30196445da6cc9a4afe998326
Source dataset
uspto-grants-2008_12
Patent number
US07462637B2

Reaction notes

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