1-Hydroxybenzotriazole → (s)-4-Tert-butoxycarbonylamino-5-[4-(3,5-dimethyl-phenyl)-piperazin-1-yl]-5-oxo-pentanoic acid tert-butyl ester

HRID 1908635Notes

Reaction equation

HRID 1908635 reaction equation
[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([OH:14])=O)[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C1C=CC2N(O)N=NC=2C=1.[CH3:32][C:33]1[CH:34]=[C:35]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:36]=[C:37]([CH3:39])[CH:38]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[C:7]([O:6][C:5](=[O:11])[CH2:4][CH2:3][C@H:2]([NH:1][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:12]([N:43]1[CH2:44][CH2:45][N:40]([C:35]2[CH:36]=[C:37]([CH3:39])[CH:38]=[C:33]([CH3:32])[CH:34]=2)[CH2:41][CH2:42]1)=[O:14])([CH3:8])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27586261-(3,5-Dimethylphenyl)piperazineHCID 6993432(2S)-5-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid

Product 1

HCID 66920414(s)-4-Tert-butoxycarbonylamino-5-[4-(3,5-dimethyl-phenyl)-piperazin-1-yl]-5-oxo-pentanoic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent3×

Procedure

75 mg of Boc-Glu(OtBu)—OH and 44 mg HOBT was dissolved in 1 ml of DMF. 52 mg of 1-(3,5-Dimethyl-phenyl)-piperazine and 97 mg of DIPEA in 1 ml of DMF was added, followed by 43 mg of EDC in 0.5 ml of DMF. The mixture was stirred for 16 h at RT (closed tube). The mixture was filtered, and the filter was washed with 20 ml ethyl acetate in two portions. The collected filtrate was washed with 20 ml of a 5% Na2CO3 solution and 20 ml of brine, dried with sodium sulfate and evaporated under reduced pressure.

Workup

  1. custom(closed tube)
  2. filtrationThe mixture was filtered
  3. washthe filter was washed with 20 ml ethyl acetate in two portions
  4. washThe collected filtrate was washed with 20 ml of a 5% Na2CO3 solution and 20 ml of brine
  5. dry with materialdried with sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ba022fde12d54b23aa50014a2bd542fd
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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