3-Aminopropionitrile → N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl)amide

HRID 1060455Notes

Reaction equation

HRID 1060455 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:3]=1[C:4]([NH:6][C@H:7]([C:25](O)=[O:26])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH3:24])=[CH:11][CH:10]=1)=[O:5].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:52]([CH2:54][CH2:55][NH2:56])#[N:53]>CN(C=O)C.O.C(Cl)CCl>[C:52]([CH2:54][CH2:55][NH:56][C:25](=[O:26])[C@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH3:24])=[CH:13][CH:14]=1)[NH:6][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:31][CH:30]=[CH:29][C:28]=1[Cl:32])#[N:53]

Participants

8

Reactant 4

HCID 16473-AminopropionitrileHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9912743(S)-2-(2,6-Dichlorobenzamido)-3-(2',6'-dimethoxy-[1,1'-biphenyl]-4-yl)propanoic acid

Product 1

HCID 54074886N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl)amide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine (0.17 g), HOBT (0.0.08 g), DIEA (0.19 mL) and 2-cyanoethylamine (0.03 mL) in DMF (5 mL) was stirred at room temperature under N2. EDC (0.14 g) was added after 10 min and the mixture was stirred at room temperature under N2. The mixture was diluted with water and extracted with EtOAc. The extract was washed successively with water, 1 N HCl, satd. NaHCO3 and brine, dried and evaporated to give 0.17 g of N-(2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine N-(2-cyanoethyl) amide. ESMS : m/z 526 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed successively with water, 1 N HCl
  3. dry with materialNaHCO3 and brine, dried
  4. customevaporated

Sources & evidence

ORD record
ord-a6f85ef36db449f68f435e9519ca8e1b
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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