Benzenepropanoic acid → HCID 11353501, compound

HRID 1358486Notes

Reaction equation

HRID 1358486 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[NH2:33][C:34]1[CH:42]=[C:41]2[C:37]([CH:38]=[CH:39][N:40]2[CH2:43][CH2:44][C@@H:45]([N:55]2[CH:59]=[C:58]([C:60]([NH2:62])=[O:61])[N:57]=[CH:56]2)[CH2:46][O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])=[CH:36][CH:35]=1>ClCCl>[Si:48]([O:47][CH2:46][C@H:45]([N:55]1[CH:59]=[C:58]([C:60]([NH2:62])=[O:61])[N:57]=[CH:56]1)[CH2:44][CH2:43][N:40]1[C:41]2[C:37](=[CH:36][CH:35]=[C:34]([NH:33][C:9](=[O:11])[CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:42]=2)[CH:38]=[CH:39]1)([C:51]([CH3:54])([CH3:52])[CH3:53])([CH3:49])[CH3:50]

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11224101HCID 11224101, compound

Product 1

HCID 11353501HCID 11353501, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3-phenylpropionic acid (46 mg, 0.304 mmol) and 1-hydroxybenzotriazol (45 mg, 0.334 mmol) in dichloromethane (5 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (52 mg, 0.334 mmol) at ice-bath temperature. The mixture was stirred for 40 minutes at room temperature. And then 1-[(R)-4-(6-aminoindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide (130 mg, 0.304 mmol) was added to the mixture at ice-bath temperature. After adding, the resulting mixture was stirred for 4 hours at room temperature. The solvent was concentrated in vacuo. And then the residue was extracted with ethyl acetate and washed with water and brine. The organic layer was dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel (6 g) column chromatography eluting with chloroform/methanol (30:1) to give 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-(3-phenylpropionylamino) indol-1-yl)-2-butyl]imidazole-4-carboxamide (170.6 mg, 100%).

Workup

  1. additionAfter adding
  2. stirringthe resulting mixture was stirred for 4 hours at room temperature
  3. concentrationThe solvent was concentrated in vacuo
  4. extractionAnd then the residue was extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel (6 g) column chromatography
  9. washeluting with chloroform/methanol (30:1)

Sources & evidence

ORD record
ord-33970537e60544daab7a046ea31c34cc
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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