1-Hydroxybenzotriazole → HCID 66855296, compound

HRID 1970507Notes

Reaction equation

HRID 1970507 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:44])[C@@H:15]([NH:25][C:26]([C:28]2[CH:32]=[C:31]([O:33][CH2:34][C:35](O)=[O:36])[N:30]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH2:65]([O:72][C:73](=[O:79])[C@@H:74]1[CH2:78][CH2:77][CH2:76][NH:75]1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>CN(C=O)C.C(Cl)CCl>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:44])[C@@H:15]([NH:25][C:26]([C:28]2[CH:32]=[C:31]([O:33][CH2:34][C:35]([N:75]3[CH2:76][CH2:77][CH2:78][C@H:74]3[C:73]([O:72][CH2:65][C:66]3[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=3)=[O:79])=[O:36])[N:30]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[N:29]=2)=[O:27])[CH2:16][CH2:17][C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733413Proline benzyl ester hydrochlorideHCID 668549334-{(S)-4-tert-butoxycarbonyl-2-[(5-carboxymethoxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid butyl ester

Product 1

HCID 66855296HCID 66855296, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.50 g 4-{(S)-4-tert-butoxycarbonyl-2-[(5-carboxymethoxy-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid butyl ester in 30 ml DMF were added 621 mg HOBt, 1.3 ml DIPEA, 778 mg EDC and 981 mg L-proline benzyl ester hydrochloride. After stirring for 12 h the solvent was evaporated, the residue dissolved in ethyl acetate and subsequently extracted with aqueous LiCl (4% w/w) and aqueous NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The crude product thus obtained was used in the subsequent reaction.

Workup

  1. customwas evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. extractionsubsequently extracted with aqueous LiCl (4% w/w) and aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a26dcff5bb494e9484677646f93f9fee
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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