Diisopropylethylamine → tert-Butyl N-[(1S,2S)-2-[5-chloro-2-(2H-1,2,3-triazol-2-yl)benzamido]cyclopentyl]carbamate

HRID 1750521Notes

Reaction equation

HRID 1750521 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N:25]2[N:29]=[CH:28][CH:27]=[N:26]2)=[C:20]([CH:24]=1)[C:21](O)=[O:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N:25]2[N:29]=[CH:28][CH:27]=[N:26]2)=[C:20]([CH:24]=1)[C:21]([NH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:22]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamineHCID 670867345-chloro-2-(2H-1,2,3-triazol-2-yl)benzoic acid2×

Product 1

HCID 118308311tert-Butyl N-[(1S,2S)-2-[5-chloro-2-(2H-1,2,3-triazol-2-yl)benzamido]cyclopentyl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 120 mg, 0.60 mmol), 5-chloro-2-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 38a; CAS number 1293284-54-4; 134 mg, 0.60 mmol), TBTU (231 mg, 0.72 mmol) and DIPEA (0.116 g, 0.9 mmol) in DMF (3 ml) was stirred at room temperature for 2 hours. The reaction was diluted with water (30 ml) and extracted with ethyl acetate (3×30 ml). The combined organics were washed with water (20 ml), brine (20 ml), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica, 0-30% ethyl acetate/n-hexane) to afford the title compound.

Workup

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. washThe combined organics were washed with water (20 ml), brine (20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica, 0-30% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-588f2d349d474c959e3d40771df6ffb7
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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