1,1'-Carbonyldiimidazole → HCID 4369082, compound

HRID 355333Notes

Reaction equation

HRID 355333 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([CH2:19][O:20][C:21]([NH:23][C@@H:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][C:26](O)=[O:27])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.[NH2:44][C:45]1[S:49][C:48]([SH:50])=[N:47][N:46]=1>C1COCC1>[C:13]1([CH2:19][O:20][C:21](=[O:22])[NH:23][C@@H:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][C:26]([NH:44][C:45]2[S:49][C:48](=[S:50])[NH:47][N:46]=2)=[O:27])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 1551704HCID 1551704, compoundHCID 178509208HCID 178509208, compound

Product 1

HCID 4369082HCID 4369082, compoundYield 14.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (0.879 g, 5.42 mmol) is added to a solution of (R)-β-[[(phenylmethoxy)carbonyl]amino]benzenepropanoic acid (1.08 g, 3.62 mmol) in 25 mL THF under N2 at room temperature and allowed to stir for 0.5 hours. Diisopropylethylamine (0.63 mL, 3.6 mmol) and 5-amino-1,3,4-thiadiazole-2-thiol (0.482 g, 3.62 mmol) are added and the reaction is stirred at ambient temperature for 18 hours. The reaction is concentrated in vacuo, diluted with 50 mL CH2Cl2, and washed with (3×25 mL) 1 M citric acid. The organic phase is dried (Na2SO4), combined with the precipitate that formed in the aqueous phase, absorbed onto silica gel and chromatographed (2-5% MeOH/CH2 Cl2). The precipitate which formed in the fractions containing product is collected and dried to afford 0.217 g product as white needles.

Workup

  1. stirringthe reaction is stirred at ambient temperature for 18 hours
  2. concentrationThe reaction is concentrated in vacuo
  3. additiondiluted with 50 mL CH2Cl2
  4. washwashed with (3×25 mL) 1 M citric acid
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. customthat formed in the aqueous phase
  7. customabsorbed onto silica gel
  8. customchromatographed (2-5% MeOH/CH2 Cl2)
  9. customThe precipitate which formed in the fractions
  10. additioncontaining product
  11. customis collected
  12. customdried

Sources & evidence

ORD record
ord-75821cd5ed5945869bf4a6b8cd6bcfbd
Source dataset
uspto-grants-1998_11
Patent number
US05830869

Reaction notes

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