1-Hydroxybenzotriazole → HCID 66855276, compound

HRID 1970481Notes

Reaction equation

HRID 1970481 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:42])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33](O)=[O:34])[N:28]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:62]([O:69][C:70]([CH:72]1[CH2:76][CH2:75][NH:74][CH2:73]1)=[O:71])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:42])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33]([N:74]3[CH2:75][CH2:76][CH:72]([C:70]([O:69][CH2:62][C:63]4[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=4)=[O:71])[CH2:73]3)=[O:34])[N:28]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13242232Benzyl pyrrolidine-3-carboxylateHCID 46186284HCID 46186284, compound

Product 1

HCID 66855276HCID 66855276, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.14 g 4-{(S)-4-tert-butoxycarbonyl-2-[(5-carboxymethoxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester in 10 ml DMF were added 719 mg HOBt, 900 mg EDC, 1.6 ml DIPEA and 1.50 g pyrrolidine-3-carboxylic acid benzyl ester hydrotrifluoroacetate. After stirring for 12 h the reaction mixture was diluted with ethyl acetate, washed with aqueous LiCl (4%) and saturated aqueous NaHCO3. The crude product obtained after evaporation of the solvent was used without further purification. Yield: 2.32 g.

Workup

  1. washwashed with aqueous LiCl (4%) and saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-af3a8e70faa743bd8a7db7d5789dd229
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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