Hydrochloric Acid → {2-[3-(tert-Butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetic acid

HRID 2389484Notes

Reaction equation

HRID 2389484 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:9][CH2:10][CH2:11][S:12][C:13]1[N:17]([CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C1COCC1.Cl>ClCCl.O>[C:1]([O:5][C:6]([N:8]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:9][CH2:10][CH2:11][S:12][C:13]1[N:17]([CH2:18][C:19]([OH:21])=[O:20])[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86620029tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate

Product 1

HCID 69313744{2-[3-(tert-Butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {2-[3-(tert-butoxycarbonyl-phenethyl-amino)-propylsulfanyl]-benzoimidazol-1-yl}-acetate (Precursor J-01b, 12.7 mg, 0.025 mmol) is suspended in an aqueous 0.2 M NaOH solution (0.67 ml). After addition of THF (1.3 ml) the resulting solution is allowed to stir overnight at rt. It is then treated with 1 M aqueous HCl (3.35 ml), water (2 ml) and dichloromethane (3 ml). The phases are separated and the dichloromethane is removed under reduced pressure. Drying under high vacuum yields the pure title compound: tR=2.12 min (LC-2), ESI-MS (neg.): m/z 470.47 [M−H]+; 1H-NMR (DMSO-d6): δ 1.31 (s, 9H, tBu), 1.88 (quint., 2H, SCH2CH2), 2.73 (m, 2H, CH2Ph), 3.24 (t, 2H), 3.28-3.36 (m, 4H), 4.94 (s, 2H, CH2CO2), 7.13 (m, 5Harom), 7.23 (t, 2Harom), 7.42-7.50 (m, 2Harom).

Workup

  1. customThe phases are separated
  2. customthe dichloromethane is removed under reduced pressure
  3. customDrying under high vacuum

Sources & evidence

ORD record
ord-a05bc3df7c1446ddac6f0f44d9f40af9
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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