1,2-Dichloroethane → HCID 86590297, compound

HRID 228135Notes

Reaction equation

HRID 228135 reaction equation
[CH:1]1([CH2:4][N:5]([S:18]([CH3:21])(=[O:20])=[O:19])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:3][CH2:2]1.[C:22]([O:26][C:27]([CH2:29][C@H:30]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=1)[C:31](O)=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[Cl:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][C@H:30]([C:31]([N:15]2[CH2:16][CH2:17][N:12]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[S:18]([CH3:21])(=[O:19])=[O:20])[CH2:13][CH2:14]2)=[O:32])[CH2:29][C:27]([O:26][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:28])=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 58996660HCID 58996660, compoundHCID 69070503HCID 69070503, compound

Product 1

HCID 86590297HCID 86590297, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (cyclopropylmethyl)(methylsulfonyl)-(2-piperazinyl-phenyl)amine (HCl salt, 2.3 g, 6.0 mmol), (2S)-3-[(tert-butyl)oxycarbonyl]-2-[(4-chlorophenyl)-methyl]propanoic acid (1.8 g, 6.02 mmol, Step 4), HOBt (0.81 g, 6.0 mmol, Novabiochem), and TEA (1.67 mL, 12.0 mmol) in 20 mL of CH2Cl2 at 0° C. was added EDC (1.73 g, 9.03 mmol, Advanced Chemtech). The reaction was warmed to RT and stirred for 12 h. The reaction was quenched with satd NaHCO3, extracted with 80 mL of EtOAc and the organic solution was washed with brine, dried over Na2SO4 and concentrated in vacuo. The compound was further purified by silica gel column chromatography (50% EtOAc in hexane) to provide 2.3 g of tert-butyl (3S)-3-[(4-chlorophenyl)-methyl]-4-(4-{2-[(cyclopropylmethyl)(methylsulfonyl)-amino]phenyl}-piperazinyl)-4-oxobutanoate as a white foam. MS (ESI, pos. ion) m/z: 590.6 (M+1). Calc'd for C30H40ClN3O5S: 589.24. Anal. Calc'd for C30H40ClN3O5S: C, 61.05; H, 6.83; N, 7.12; Cl, 6.01. Found: C, 60.91; H, 6.69; N, 7.09; Cl, 6.16.

Workup

  1. customThe reaction was quenched with satd NaHCO3
  2. extractionextracted with 80 mL of EtOAc
  3. washthe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe compound was further purified by silica gel column chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-006beb1a54be429fa47d50a2105d6c88
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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