1-Hydroxybenzotriazole → HCID 178451022, compound

HRID 1908631Notes

Reaction equation

HRID 1908631 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][CH2:8][C@H:9]([NH2:28])[C:10](=[O:27])[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[OH:40][C:41]1[N:45]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[N:44]=[C:43]([C:52](O)=[O:53])[CH:42]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:29])[CH2:7][CH2:8][C@H:9]([NH:28][C:52]([C:43]1[CH:42]=[C:41]([OH:40])[N:45]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[N:44]=1)=[O:53])[C:10](=[O:27])[N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=2)[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66920231HCID 66920231, compoundHCID 178524628HCID 178524628, compound

Product 1

HCID 178451022HCID 178451022, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2.2 g of (S)-4-Amino-5-oxo-5-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-pentanoic acid tert-butyl ester in 30 ml of DMF, 892 mg of HOBT, 1.08 g of 5-Hydroxy-1-phenyl-1H-pyrazole-3-carboxylic acid 1.12 g EDC Hydrochlorid and 1.90 ml DIPEA was added. After 3 h at RT the mixture was diluted with ethyl acetate and washed with saturated sodium hydrogen carbonate solution. Drying of the organic layer over sodium sulfate and evaporation under reduced pressure afforded a brownish powder that was purified by chromatography over silica gel eluting with ethyl acetate/heptane 1:1 to 100% ethyl acetate to give 2.7 g of the desired product. Yield: 2.7 g MS (ES+): m/e=416.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution
  2. dry with materialDrying of the organic layer over sodium sulfate and evaporation under reduced pressure
  3. customafforded a brownish powder that
  4. customwas purified by chromatography over silica gel eluting with ethyl acetate/heptane 1

Sources & evidence

ORD record
ord-007dd9ca159d454da922d169be7a66a3
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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