Triethylamine → Tert-butyl{2-[3-(pentanoyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate

HRID 2389488Notes

Reaction equation

HRID 2389488 reaction equation
[Cl-].[C:2]([O:6][C:7]([CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[S:19][CH2:20][CH2:21][CH2:22][NH2+:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].CCN(CC)CC.[C:39](Cl)(=[O:44])[CH2:40][CH2:41][CH2:42][CH3:43]>ClCCCl>[C:2]([O:6][C:7](=[O:8])[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[S:19][CH2:20][CH2:21][CH2:22][N:23]([C:39](=[O:44])[CH2:40][CH2:41][CH2:42][CH3:43])[CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 69318458[3-(1-tert-Butoxycarbonylmethyl-1H-benzoimidazol-2-ylsulfanyl)-propyl]-phenethyl-ammonium chloride

Product 1

HCID 90860692Tert-butyl{2-[3-(pentanoyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

[3-(1-tert-Butoxycarbonylmethyl-1H-benzoimidazol-2-ylsulfanyl)-propyl]-phenethyl-ammonium chloride (Precursor U-01b, 11.6 mg, 0.025 mmol) and Et3N (12.2 mg, 17.2 μl, 0.1 mmol) are dissolved in 1,2-dichloroethane (0.2 ml). To this solution is added valerylchloride (9 mg, 8.95 μl, 0.075 mmol) and the stirring is continued for 2 h. Then 1,2-dichloroethane (0.4 ml) and tris-(2-aminoethyl)amine polystyrene (3.4 mmol/g, 22 mg, 0.075 mmol) are added. After 30 min of shaking the resin is filtered off. Then methylisocyanate polystyrene (2.5 mmol/g, 30 mg, 0.075 mmol) is added as well as 1,2-dichloroethane (0.5 ml) and the resulting suspension is stirred for 2 h. It is filtered and the organic filtrate is washed with an aqueous KH2PO4 solution (pH=4) and water. Finally the organic phase is dried over Na2SO4 and evaporated to dryness yielding the title compound: tR=2.62 min (LC-2), ESI-MS (pos.): m/z 510.49 [M+H]+; 1H-NMR (DMSO-d6 at 100° C.): δ (ppm) 0.80 (t, 3H, CH2CH3), 1.19 (m, 2H, CH2CH3), 1.37 (m, 2H, CH2CH2CH3), 1.40 (s, 9H, tBu), 1.91 (m, 2H, CH2CH2N), 2.08 (m, 1H, COCHa), 2.24 (m, 1H, COCHb), 2.71-2.83 (m, 2H, CH2Ph), 3.30 (m, 2H), 3.32-3.43 (m, 4H), 4.98 (m, 2H, CH2CO2), 7.12-7.26 (m, 7 Harm), 7.50 (m, 2Harom).

Workup

  1. filtrationis filtered off
  2. stirringthe resulting suspension is stirred for 2 h
  3. filtrationIt is filtered
  4. washthe organic filtrate is washed with an aqueous KH2PO4 solution (pH=4) and water
  5. dry with materialFinally the organic phase is dried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-eb87c043442c46598fef6a3e57eac49d
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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