1,1'-Carbonyldiimidazole → HCID 59042565, compound

HRID 2414336Notes

Reaction equation

HRID 2414336 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:25]([OH:27])=O)[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[CH2:17][O:16][C:15]2=[O:24])[CH2:10][CH2:9]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:41][C@@H:42]([C:46]([NH2:48])=[O:47])[CH:43]([CH3:45])[CH3:44].C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[NH2:48][C:46]([C@H:42]([NH:41][C:25]([C:4]1[CH:5]=[N:6][C:7]([N:8]2[CH2:9][CH2:10][CH:11]([N:14]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][O:16][C:15]3=[O:24])[CH2:12][CH2:13]2)=[C:2]([Cl:1])[CH:3]=1)=[O:27])[CH:43]([CH3:45])[CH3:44])=[O:47]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 22644584HCID 22644584, compoundHCID 53486046(2R)-2-amino-3-methylbutanamide hydrochloride

Product 1

HCID 59042565HCID 59042565, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product of step (i) (0.14 g) was dissolved in 1-methyl-2-pyrrolidinone (4 ml) and to this solution was added carbonyldiimidazole (0.064 g) the mixture was stirred at room temperature for 1 h and then treated with D-valinamide hydrochloride (0.11 g) and N,N-diisopropylethylamine (0.10 g). After stirring for 18 h at room temperature the mixture was partitioned between aqueous sodium bicarbonate and ethyl acetate, the organic layer was washed with water, dried and evaporated under reduced pressure. The resultant solid was washed with ethyl acetate to yield 0.06 g of product.

Workup

  1. stirringAfter stirring for 18 h at room temperature the mixture
  2. customwas partitioned between aqueous sodium bicarbonate and ethyl acetate
  3. washthe organic layer was washed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. washThe resultant solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-56e58f7e856442f3be6a3910c741d571
Source dataset
uspto-grants-2004_11
Patent number
US06812226B2

Reaction notes

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