1-Hydroxybenzotriazole → 2-[4-(2-Cyano-phenyl)-piperazine-1-carbonyl]-4-[(benzyl)-(2,2,2-trichloroethoxycarbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 490577Notes

Reaction equation

HRID 490577 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:13]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])[CH2:10][CH:9]1[C:29]([OH:31])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[C:42]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1)#[N:43].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCN(CC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:13]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]([O:16][CH2:17][C:18]([Cl:19])([Cl:21])[Cl:20])=[O:15])[CH2:10][CH:9]1[C:29]([N:53]1[CH2:52][CH2:51][N:50]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[C:42]#[N:43])[CH2:55][CH2:54]1)=[O:31])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735875N-(2-Cyanophenyl)piperazineHCID 675477354-[(Benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester

Product 1

HCID 675465492-[4-(2-Cyano-phenyl)-piperazine-1-carbonyl]-4-[(benzyl)-(2,2,2-trichloroethoxycarbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[(benzyl)-(2,2,2-trichloro-ethoxycarbonyl)-amino]-pyrrolidine-1,2-dicarboxylicacid 1-tert-butyl ester, HOBt, 1-(2-cyanophenyl)piperazine in DCM are added Et3N and EDC.HCl. The mixture is stirred overnight, then washed with citric acid, Na2CO3, brine, dried and concentrated to give 2-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-4-[(benzyl)-(2,2,2-trichloroethoxycarbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester (21)

Workup

  1. washwashed with citric acid, Na2CO3, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6768c854e9074a8aa0a36eb51283fdf3
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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