Structure of 6-(Tritylthio)hexanoic acid
CAS No.: 80441-55-0
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CAS No. : | 80441-55-0 |
Formula : | C25H26O2S |
M.W : | 390.54 |
SMILES Code : | O=C(O)CCCCCSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3 |
MDL No. : | MFCD11226801 |
InChI Key : | ILAPAFBLFPIIBL-UHFFFAOYSA-N |
Pubchem ID : | 21480969 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃; for 12h; | Compound 69 was synthesized from compound 43 (FIG. 13A). 6-Tritylsulfanyl-hexanoic acid was coupled to 43 via standard EDC/HOBt coupling. To a solution of 43 (140 mg, 34 mumol) and 6-tritylsulfanyl-hexanoic acid (67 mg, 5 equivalents) in dichloromethane (2 mL) was added hydroxybenzotriazole (23 mg, 5 equivalents) and triethlamine (24 muL, 5 equivalents). The solution was cooled to ice bath temperature and 1-ethyl-3-(3-dimethylamino-propyl)-carbodiimide(EDC) (33 mg, 5 equivalents) was added. The solution was allowed to warm to room temperature and stirred at this temperature for 12 hours. The reaction mixture was diluted with dichloromethane (10 mL) and decanted into water (10 mL). The aqueous phase was extracted with dichloromethane (3×20 mL). The combined organic layers were then washed with 1 N aqueous hydrochloric acid (3×30 mL), saturated aqueous bicarbonate solution (1×30 mL) and brine (1×10 mL). The solution was dried over magnesium sulfate and concentrated. Flash column chromatography (DCM/MeOH 10:1) gave the intermediate product as a colorless foam shaped solid. (145 mg, 96%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | Mmt protected intermediate 2b (3.18 g, 9.56 mmol) was dissolved in DCM (30 mL). 6- (Tritylthio)-hexanoic acid (4.48 g, 1 1.5 mmol), PyBOP (5.67 g, 10.9 mmol) and DIPEA (5.0 mL, 28.6 mmol) were added and the mixture was stirred for 30 min at rt. The solution was diuted with diethyl ether (250 mL), washed 3 x with brine/0.1 M NaOH 30/1 (v/v) and once with brine. The organic phase was dried over Na2SO4and the solvent was removed in vacuo. 2c was purified using flash chromatography.Yield: 5.69 g (85 %)MS: m/z 705.4 = [M+H]+, (calculated monoisotopic mass = 704.34). |
85% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | Mmt protected intermediate 2b (3.18 g, 9.56 mmol) was dissolved in DCM (30 mL). 6- (Tritylthio)-hexanoic acid (4.48 g, 11.5 mmol), PyBOP (5.67 g, 10.9 mmol) and DIPEA (5.0 mL, 28.6 mmol) were added and the mixture was stirred for 30 min at rt. The solution was diuted with diethyl ether (250 mL), washed 3 x with brine/0.1 M NaOH 30/1 (v/v) and once with brine. The organic phase was dried over Na2S04 and the solvent was removed in vacuo. 2c was purified using flash chromatography. Yield: 5.69 g (85 %) MS: m/z 705.4 = [M+H]+, (calculated monoisotopic mass = 704.34). |
85% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | Mmt protected intermediate 2b (3.18 g, 9.56 mmol) was dissolved in DCM (30 mL). 6- (Tritylthio)-hexanoic acid (4.48 g, 11.5 mmol), PyBOP (5.67 g, 10.9 mmol) and DIPEA (5.0 mL, 28.6 mmol) were added and the mixture was stirred for 30 min at rt. The solution was diuted with diethyl ether (250 mL), washed 3 x with brine/0.1 M NaOH 30/1 (v/v) and once with brine. The organic phase was dried over Na2S04 and the solvent was removed in vacuo. 2c was purified using flash chromatography. Yield: 5.69 g (85 %) MS: m/z 705.4 = [M+H]+, (calculated monoisotopic mass = 704.34). |
85% | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | Mmt protected intermediate 2b (3.18 g, 9.56 mmol) was dissolved in DCM (30 mL). 6- (Tritylthio)-hexanoic acid (4.48 g, 11.5 mmol), PyBOP (5.67 g, 10.9 mmol) and DIPEA (5.0 mL, 28.6 mmol) were added and the mixture was stirred for 30 mm at rt. The solution was diuted with diethyl ether (250 mL), washed 3 x with brine/0.1 M NaOH 30/1 (v/v) and oncewith brine. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo.2c was purified using flash chromatography.Yield: 5.69g(85%)MS: m/z 705.4 = [M+Hf?, (calculated monoisotopic mass = 704.34). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | The Mmt-protected amine (3.18 g, 9.56 mmol) was dissolved in anhydrous DCM (30 mL). 6- (S'-Tritylmercapto)hexanoic acid (4.48 g, 11.47 mmol), PyBOP (5.96 g, 11.47 mmol) and DIPEA (5.0 mL, 28.68 mmol) were added and the mixture was agitated for 30 min at RT. The solution was diluted with diethyl ether (250 mL) and washed three times with 30/1 (v/v) brine/0.1 M NaOH solution (50 mL each) and once with brine (50 mL). The organic phase was dried over Na2S04 and volatiles were removed under reduced pressure. Amide was purified by flash chromatography eluting with heptane/ethyl acetate containing 0.02 % (v/v) diethy lmethy lamine . Yield: 5.69 g (8.07 mmol). MS: m/z 705.4 = [M+H]+ (MW = 705.0). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | The Mmt-protected amine (3.18 g, 9.56 mmol) was dissolved in anhydrous DCM (30 mL). 6- (S'-Tritylmercapto)hexanoic acid (4.48 g, 11.47 mmol), PyBOP ( 5.96 g, 11.47 mmol) and DIPEA (5.0 mL, 28.68 mmol) were added and the mixture was agitated for 30 min at RT. The solution was diluted with diethyl ether (250 mL) and washed three times with 30/1 (v/v) brine/0.1 M NaOH solution (50 mL each) and once with brine (50 mL). The organic phase was dried over Na2S04 and volatiles were removed under reduced pressure. Amide was purified by flash chromatography eluting with heptane/ethyl acetate containing 0.02 % (v/v) diethy lmethy lamine . Yield: 5.69 g (8.07 mmol). MS: m/z 705.4 = [M+H]+ (MW = 705.0). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | The Mmt-protected intermediate (3.18 g, 9.56 mmol) was dissolved in anhydrous DCM (30 mL). 6-(Tritylmercapto)-hexanoic acid (4.48 g, 11.47 mmol), PyBOP (5.67 g, 11.47 mmol) and DIEA (5.0 mL, 28.68 mmol) were added and the mixture was agitated for 30 min at RT. The solution was diluted with diethyl ether (250 mL) and washed three times with 30/1 (v/v) brine/0.1 M NaOH solution (50 mL each) and once with brine (50 mL). The organic phase was dried over Na2SO4 and volatiles were removed under reduced pressure. 5a was purified by flash chromatography. (0448) Yield: 5.69 g (8.09 mmol). (0449) MS: m/z 705.4=[M+H]+ (calculated=705.0). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | The Mmt-protected intermediate (3.18 g, 9.56 mmol) was dissolved in anhydrous DCM (30 mL). 6-(Tritylmercapto)-hexanoic acid (4.48 g, 11.47 mmol), PyBOP (5.67 g, 11.47 mmol) and DIEA (5.0 mL, 28.68 mmol) were added and the mixture was agitated for 30 min at RT. The solution was diluted with diethyl ether (250 mL) and washed three times with 30/1 (v/v) brine/0.1 M NaOH solution (50 mL each) and once with brine (50 mL). The organic phase was dried over Na2SO4 and volatiles were removed under reduced pressure. 5a was purified by flash chromatography. (0502) Yield: 5.69 g (8.09 mmol). (0503) MS: m/z 705.4=[M+H]+ (calculated=705.0). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | The Mmt-protected amine (3.18 g, 9.56 mmol) was dissolved in anhydrous DCM (30 mE). 6-(S-Tritylmercapto) hexanoic acid (4.48 g, 11.47 mmol), PyBOP (5.96 g, 11.47mmol) and DIPEA (5.0 mE, 28.68 mmol) were added and the mixture was agitated for 30 mm at RT. The solution was diluted with diethyl ether (250 mE) and washed three times with 30/1 (v/v) brine/0.1 M NaOH solution (50 mE each) and once with brine (50 mE). The organic phase was dried over Na2504 and volatiles were removed under reduced pressure. Amide was purified by flash chromatography eluting with heptane/ethyl acetate containing 0.02% (v/v) diethylmethylamine. https://imc-apps:8002Yield: 5.69 g (8.07 mmol).MS: m/z 705.4=[M+H] (MW=705.0). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | The Mmt-protected amine (3.18 g, 9.56 mmol) was dissolved in anhydrous DCM (30 mL). 6-(S-Tritylmercapto) hexanoic acid (4.48 g, 11.47 mmol), PyBOP (5.96 g, 11.47 mmol) and DIPEA (5.0 mL, 28.68 mmol) were added and the mixture was agitated for 30 mm at RT. The solution was diluted with diethyl ether (250 mL) and washed three times with 30/1 (v/v) brine/0.1 M NaOH solution (50 mL each) and once with brine (50 mL). The organic phase was dried over Na2504 and volatiles were removed under reduced pressure. Amide was purified by flash chromatography eluting with heptane/ethyl acetate containing 0.02% (v/v) diethylmethylamineYield: 5.69 g (8.07 mmol).MS: mlz 705.4=[M+H] (MW=705.0). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | The Mmt-protected intermediate (3.18 g, 9.56mmol) was dissolved in anhydrous DCM (30 mL). 6-(STritylmercapto)hexanoic acid (4.48 g, 11.47 mmol), PyBOP(5.67 g, 11.47 mmol) and DIPEA (5.0 mL, 28.68 mmol)were added and the mixture was agitated for 30 min at RT.The solution was diluted with diethyl ether (250 mL) and washed three times with 30/1 (v/v) brine/0.1 M NaOHsolution (50 mL each) and once with brine (50 mL). Theorganic phase was dried over Na2S04 and volatiles wereremoved under reduced pressure. Sa was purified by flashchromatography. Yield: 5.69 g (8.09 mmol). MS: m/z 705.4=[M+Ht (MW calculated=705.0). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | The Mmt-protected intermediate (3.18 g, 9.56 mmol) was dissolved in anhydrous DCM (30 mL). 6-(S-Tritylmercapto)hexanoic acid (4.48 g, 11.47 mmol), PyBOP (5.67 g, 11.47 mmol) and DIPEA (5.0 mL, 28.68 mmol) were addedand the mixture was agitated for 30 min at RT. The solution was diluted with diethyl ether (250 mL) and washed threetimes with 30/1 (v/v) brine/0.1 M NaOH solution (50 mL each) and once with brine (50 mL). The organic phase was driedover Na2SO4 and volatiles were removed under reduced pressure. 5a was purified by flash chromatography.Yield: 5.69 g (8.09 mmol).MS: m/z 705.4 = [M+H]+ (MW calculated = 705.0). |
5.69 g | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 0.5h; | Mmt-protected intermediate (3.18 g, 9.56 mmol) was used in the next step without further purification.The Mmt-protected intermediate (3.18 g, 9.56 mmol) was dissolved in anhydrous DCM (30 ml_). 6-(S-Tritylmercapto)hexanoic acid (4.48 g, 11.47 mmol), PyBOP (5.67 g, 11.47 mmol) and DIPEA (5.0 ml_, 28.68 mmol) were added and the mixture was agitated for 30 min at RT. The solution was diluted with diethyl ether (250 ml_) and washed three times with 30/1 (v/v) brine/0.1 M NaOFI solution (50 ml_ each) and once with brine (50 ml_). The organic phase was dried over Na2S04 and volatiles were removed under reduced pressure. 5a was purified by flash chromatography.Yield: 5.69 g (8.09 mmol).MS: m/z 705.4 = [M+H]+ (MW calculated = 705.0). |