Dichloromethane → HCID 86583993, compound

HRID 1859592Notes

Reaction equation

HRID 1859592 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([OH:13])=O.[NH2:14][C@H:15]([C:19]([NH:21][C@H:22]([CH:35]=[O:36])[CH2:23][C:24](=[N:30][NH:31][C:32]([NH2:34])=[O:33])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:20])[CH:16]([CH3:18])[CH3:17].C(Cl)Cl.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOCC>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:14][C@H:15]([C:19]([NH:21][C@H:22]([CH:35]=[O:36])[CH2:23][C:24](=[N:30][NH:31][C:32]([NH2:34])=[O:33])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:20])[CH:16]([CH3:17])[CH3:18])=[O:13]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 86583994HCID 86583994, compound

Product 1

HCID 86583993HCID 86583993, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

1-Methylindole-2-carboxylic acid (88 mg, 0.5 mmol) and (3S)-3-(Valinyl)amino-4-oxobutanoic acid, t-butyl ester semicarbazone (163 mg, 0.5 mmol) were dissolved in DMF (1 mL) and methylene chloride (2 mL) then both DMAP (61 mg, 0.50 mmol) and EDAC (134 mg, 0.7 mmol) were added to the solution under a nitrogen atmosphere at 0° C. Stirring was continued for 1 hour at 0° C. and an additional 4 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution. The ethyl acetate solution was washed successively with 5% KHSO4 solution, saturated sodium bicarbonate solution and brine solutions, dried over sodium sulfate, and concentrated to give a yellow foam. Trituration of the foam with ether afforded the title product as a slightly yellow powder (203 mg, 86%). TLC: (methanol/methylene chloride: 5/95, silica gel): Rf=0.17.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 5% KHSO4 solution
  2. washThe ethyl acetate solution was washed successively with 5% KHSO4 solution, saturated sodium bicarbonate solution and brine solutions
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a yellow foam

Sources & evidence

ORD record
ord-f838f0cd354d473194457cbd71425a0d
Source dataset
uspto-grants-2003_03
Patent number
US06528506B2

Reaction notes

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