1,2-Dichloroethane → HCID 71060184, compound

HRID 337204Notes

Reaction equation

HRID 337204 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15]([NH:17][CH:18]1[CH2:23][CH2:22][N:21]([S:24]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=O)=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:20][CH2:19]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(Cl)CCl.[CH:40]1[CH:41]=[CH:42]C2N(O)N=[N:46][C:44]=2[CH:45]=1.N1CCCCC1>C(Cl)Cl>[C:10]([O:14][C:15](=[O:16])[NH:17][CH:18]1[CH2:19][CH2:20][N:21]([S:24]([C:27]2[CH:28]=[CH:29][C:30]([C:31]([N:46]3[CH2:42][CH2:41][CH2:40][CH2:45][CH2:44]3)=[O:33])=[CH:34][CH:35]=2)(=[O:25])=[O:26])[CH2:22][CH2:23]1)([CH3:12])([CH3:13])[CH3:11]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 71060138HCID 71060138, compound

Product 1

HCID 71060184HCID 71060184, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.36 ml, 2.1 mmol) was added in one portion to a stirred solution of 4-(4-tert-butoxycarbonylamino-piperidine-1-sulfonyl)-benzoic acid (0.2 g, 0.52 mmol), EDC (0.2 g, 1.04 mmol) and HOBT (0.16 g, 1.04 mmol) in DCM (5 ml) at room temperature. The mixture was stirred at room temperature for 10 minutes before piperidine (0.07 ml, 0.78 mmol) was added in one portion and stirring continued for 24 hours. After this time the mixture was diluted with DCM (50 ml), washed sequentially with saturated sodium bicarbonate (20 ml), water (20 ml) and brine (20 ml). The organic layer was separated, dired (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 0 to 2% MeOH in DCM) to give the title compound (0.17 g, 74% yield) as a white powder. δH (250 MHz, MeOD) 7.89-8.06 (m, 2 H) 7.67-7.82 (m, 2 H) 3.68-3.93 (m, 4 H) 2.54-2.75 (m, 2 H) 2.02 (dd, J=12.94, 3.35 Hz, 2 H) 1.76-1.91 (m, 4 H) 1.56-1.75 (m, 4 H) 1.53 (s, 9 H). Tr=1.94 min m/z (ES+) (M+Na+) 474.

Workup

  1. additionwas added in one portion
  2. washwashed sequentially with saturated sodium bicarbonate (20 ml), water (20 ml) and brine (20 ml)
  3. customThe organic layer was separated
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (elution: 0 to 2% MeOH in DCM)

Sources & evidence

ORD record
ord-26819838f6cf436ea5f0a5b564ed835e
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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