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Chemical Structure| 3262-72-4 Chemical Structure| 3262-72-4
Chemical Structure| 3262-72-4

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Boc-Ser-OH is a serine derivative, commonly used in biochemical research and drug synthesis.

Synonyms: (S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid

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Product Details of Boc-Ser-OH

CAS No. :3262-72-4
Formula : C8H15NO5
M.W : 205.21
SMILES Code : O=C(O)[C@@H](NC(OC(C)(C)C)=O)CO
Synonyms :
(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid
MDL No. :MFCD00037243
InChI Key :FHOAKXBXYSJBGX-YFKPBYRVSA-N
Pubchem ID :98766

Safety of Boc-Ser-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Boc-Ser-OH

* 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.

  • Downstream synthetic route of [ 3262-72-4 ]

[ 3262-72-4 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 3262-72-4 ]
  • [ 74-88-4 ]
  • [ 51293-47-1 ]
YieldReaction ConditionsOperation in experiment
28% A. (S)-2-(tert-Butoxycarbonylamino)-3-methoxypropanoic acid A sodium methanolate (NaOMe) solution was prepared by slowly adding MeOH (50 mL) to a suspension of sodium hydride (60percent in mineral oil, 28 g, 0.71 mol) in dry THF (1.2 L) at 0° C. The resulting mixture was stirred at RT for 2 h. A portion of the NaOMe solution (320 mL) was added to (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (36 g, 175 mmol) in dry THF (1.6 L), and the mixture was stirred at RT for 1 h. Methyl iodine (16 mL) was then added and the mixture was stirred at RT for 1 h. Another aliquot of NaOMe solution (540 mL) was added and the reaction mixture stirred at RT for 1 h. Additional methyl iodine (38 mL) in THF (200 mL) was added and the reaction mixture was stirred at RT for 36 h. Following reaction, the mixture was concentrated and the residue was dissolved in water and washed with diethyl ether (2.x.100 mL). The aqueous layer was acidified to pH 2 by the addition of solid citric acid and was extracted with EtOAc (3.x.200 mL) and dried over Na2SO4. The organic phase was concentrated, and the residue was dissolved in water and extracted with DCM (4.x.150 mL). The organic layers were combined and concentrated to give the title compound as an oil, which was used without further purification (10.9 g, 28percent).
  • 3
  • [ 3262-72-4 ]
  • [ 2886-33-1 ]
  • [ 131574-38-4 ]
  • 5
  • [ 3262-72-4 ]
  • [ 20845-17-4 ]
  • N-tert-butyloxycarbonyl-L-seryl-L-alanine allyl ester [ No CAS ]
  • 6
  • [ 506-68-3 ]
  • [ 15761-38-3 ]
  • [ 3262-72-4 ]
  • [ 53308-95-5 ]
  • 4-methylbenzhydrylamine resin [ No CAS ]
  • (R)-2-((S)-2-Imino-4-methyl-imidazolidin-1-yl)-3-((S)-2-imino-5-propyl-imidazolidin-1-yl)-propan-1-ol [ No CAS ]
  • 7
  • [ 3262-72-4 ]
  • [ 98541-64-1 ]
  • 9
  • [ 3262-72-4 ]
  • enantiomeric (R)-3-amino-2-oxetanone salt [ No CAS ]
  • [ 98541-64-1 ]
YieldReaction ConditionsOperation in experiment
The enantiomeric (R)- 3-amino-2-oxetanone salt was produced in an identical manner from BOC-D-serine beta-lactone prepared from BOC-D-serine.
  • 10
  • [ 3262-72-4 ]
  • [ 3290-06-0 ]
  • 2-tert-Butoxycarbonylamino-3-(3,5-dichloro-benzyloxy)-propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In diethyl ether; N,N-dimethyl-formamide; mineral oil; E. 2-tert-Butoxycarbonylamino-3-(3,5-dichloro-benzyloxy)-propionic acid To a stirred solution of N-t-butoxycarbonyl-D-serine (10.0 g, 48.7 mol) in N,N-dimethylformamide (150 mL) at about 0° C. was added sodium hydride (4.0 g, 60percent dispersion in mineral oil, 99.84 mmol) portionwise. The mixture was stirred for about 30 minutes, and then a solution of <strong>[3290-06-0]1,3-dichloro-5-chloromethyl-benzene</strong> (9.5 mL, 48.7 mmol) in ethyl ether (40 mL) was added. The reaction was allowed to slowly warm to room temperature overnight. The reaction was then quenched with 1N NaOH, the mixture extracted three times with dichloromethane. The combined organic layers were then washed three times with water, 1N, HCl, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give crude product. The original basic aqueous layer was then acidified to about pH 4 with 1N HCl, and the mixture was extracted three times with dichloromethane. These three organic layers were combined and washed three times each with water and brine then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give an additional 620 mg of crude product. Both product fractions were combined and purified by silica gel chromatography using 5percent methanol/chloroform as eluent and yielded the title compound of part 1-E (12.39 g, 70percent): -APcl MS (M-1)- 363, (M-3)- 361; 1H NMR=400 MHz (CDCl3) delta: 7.13 (arom, s, 3H), 5.42 (NH, d, 1H), 4.50 (CHCO2H, m, 1H), 4.45 (PhCH2O, s, 2H), 3.82 (CH2OBz, d of d, 2H), 1.43 (BOC, s, 9H).
  • 11
  • [ 3262-72-4 ]
  • [ 125414-41-7 ]
  • 14
  • [ 3262-72-4 ]
  • [ 100-46-9 ]
  • [ 880468-89-3 ]
  • 15
  • [ 3262-72-4 ]
  • [ 68176-57-8 ]
  • [ 1449474-75-2 ]
YieldReaction ConditionsOperation in experiment
73 mg Preparation 12 (R)-ferf-Butyl (1 -(5-( e/t-butyl)-1 H-benzo[d1imidazol-2-yl)-2-hvdroxyethyl)carbamate (S)-2-((fe/t-Butoxycarbonyl)amino)-3-hydroxypropanoic acid (226 mg, 1 .10 mmol) was dissolved in N,N-dimethylformamide (5 ml_) and 1 -[bis(dimethylamino)methylene]-1 H- 1 ,2,3-triazolo[4,5-b]pyridinium-3-oxid-hexafluorophosphate (440 mg, 1 .10 mmol) was added. The reaction was stirred for 10 minutes then 4-(terf-butyl)benzene-1 ,2-diamine (164 mg, 1 .00 mmol) was added and the reaction mixture stirred for 18 hours. The reaction mixture was diluted with water and extracted twice with ethyl ether. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The residue was dissolved in 1 ,2-dichloroethane and anhydrous magnesium sulfate was added. The reaction was stirred at 65°C for 18 hours to complete the dehydration. The reaction mixture was filtered and loaded directly onto a 4g silica gel column for purification. The column was eluted with 0-10percent methanol in dichloromethane to afford 73 mg of product as a white solid. 1H NMR (400MHz, DMSO-d6): delta ppm 1 .33 (s, 9H), 1 .40 (s, 9H), 3.72 (m, 2H), 4.76 (m, 1 H), 4.95 (t, 1 H), 7.03, (m, 1 H), 7.21 (m, 1 H), 7.34-7.52 (m, 2H), 1 1 .95 (m, 1 H). LCMS Rt = 1 .03 minutes MS m/z 334 [M+H]+ (R)-ferf-Butyl (1 -(5-( e/t-butyl)-1 H-benzo[d1imidazol-2-yl)-2-hvdroxyethyl)carbamate (S)-2-((fe/t-Butoxycarbonyl)amino)-3-hydroxypropanoic acid (226 mg, 1 .10 mmol) was dissolved in N,N-dimethylformamide (5 ml_) and 1 -[bis(dimethylamino)methylene]-1 H- 1 ,2,3-triazolo[4,5-b]pyridinium-3-oxid-hexafluorophosphate (440 mg, 1 .10 mmol) was added. The reaction was stirred for 10 minutes then 4-(terf-butyl)benzene-1 ,2-diamine (164 mg, 1 .00 mmol) was added and the reaction mixture stirred for 18 hours. The reaction mixture was diluted with water and extracted twice with ethyl ether. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The residue was dissolved in 1 ,2-dichloroethane and anhydrous magnesium sulfate was added. The reaction was stirred at 65°C for 18 hours to complete the dehydration. The reaction mixture was filtered and loaded directly onto a 4g silica gel column for purification. The column was eluted with 0-10percent methanol in dichloromethane to afford 73 mg of product as a white solid. 1H NMR (400MHz, DMSO-d6): delta ppm 1 .33 (s, 9H), 1 .40 (s, 9H), 3.72 (m, 2H), 4.76 (m, 1 H), 4.95 (t, 1 H), 7.03, (m, 1 H), 7.21 (m, 1 H), 7.34-7.52 (m, 2H), 1 1 .95 (m, 1 H). LCMS Rt = 1 .03 minutes MS m/z 334 [M+H]+
  • 16
  • [ 3262-72-4 ]
  • [ 68176-57-8 ]
  • C18H29N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; HATU; In N,N-dimethyl-formamide; at 60℃; for 16h; General procedure: Step 1 To 4-te/t-butyl-1 ,2-diaminobenzene (100 pmol, 1 eq) was added a solution of Monomer B in DMF (0.2M, 500 muIota_, 100 mupiiotaomicronIota, 1 eq) followed by TEA (28 muIota_, 200 mupiiotaomicronIota, 2 eq) and a solution of HATU in DMF (0.2 M, 500muIota_, 100 mupiiotaomicronIota, 1 eq). The reaction was shaken at 60°C for 16 hours before cooling and concentrating in vacuo to afford crude uncyclised Intermediate AB. Step 2 To crude uncyclised Intermediate AB was added acetic acid (1000 muIota_) and the reaction was shaken at 80°C for 1 hour. The reaction was cooled, concentrated in vacuo and dissolved in DMSO. The solution was filtered and purified using preparative HPLC to afford Intermediate AB. Step 3 To Intermediate AB was added DCM (1800 muiotatauiotaomicronIota) followed by 4M HCI in dioxane (200 muIota_) and the reaction was shaken at 30°C for 1 .5 hours. The reaction was concentrated in vacuo to afford the final compounds as their HCI salts. Prepared according to Library Protocol 2 using N-Boc-L-serine with purification by preparative HPLC: Preparative HPLC: Phenomenex Gemini C18; 250x21 .2mmx10um; Acetonitrile :NH4OH eluting with 41 -71 percent MeCN over 8.5 minute gradient time. Flow rate 30 mL/min.
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 60℃; for 16h; General procedure: The title compounds were prepared in parallel format using thefollowing protocol: Step 1: To 4-alkyl-1, 2-diaminobenzene (100 mumol,1 eq) was added a solution of the required amino acid in DMF (0.2 M,500 muL, 100 mumol, 1 eq) followed by TEA (28 muL, 200 mumol, 2 eq) and asolution of HATU in DMF (0.2 M, 500 muL, 100 mumol, 1 eq). The reactionwas shaken at 60 °C for 16 h before cooling and concentrating in vacuoto afford crude uncyclised intermediate. Step 2: To crude uncyclizedintermediate was added acetic acid (1000 muL) and the reaction wasshaken at 80 °C for 1 h. The reaction was cooled, concentrated in vacuoand dissolved in DMSO. The solution was filtered and purified usingpreparative HPLC to afford the intermediate benzimidazole. Step 3: Tothe intermediate benzimidazole was added CH2Cl2 (1800 mumol) followedby 4M HCI in dioxane (200 muL) and the reaction was shaken at30 °C for 1.5 h. The reaction was concentrated in vacuo to afford productas the HCl salt.
  • 17
  • [ 75-18-3 ]
  • [ 3262-72-4 ]
  • [ 51293-47-1 ]
YieldReaction ConditionsOperation in experiment
240.3 kg With sodium hydroxide; at 10℃; for 44h;Large scale; Example 2 Synthesis of (S)-2-((tert-butoxycarbonyl)amino)-3-methoxypropanoic acid (0033) (0034) 45percent 4 NaOH (746.3 kg; 8.40 kmoles) and DMS (1053.8 kg; 8.36 kmoles) were added to the reaction mixture below 10° C. over 38 h and for an additional 6 h to complete the reaction. 20percent 9 NH4OH (20.0 kg) was added to quench the reaction in the reaction mixture. The pH value was adjusted by 10 citric acid monohydrate (55.8 kg) and 32percent 11 HCl (180 kg) to around 3. The 12 product was extracted by toluene (1165 L) twice, and the organic layer was washed by 1percent NaOH (40 L) and H2O (39 L×2). The organic layer was concentrated, and stripped by IPA as oil residue (240.3 kg)
  • 18
  • [ 19064-24-5 ]
  • [ 3262-72-4 ]
  • (S)-2-(tert-butoxycarbonylamino)-3-(3-fluoro-2-nitrophenoxy)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% To a suspension of NaH (55 wt %, 823 mg, 18.9 mmol) in DMF (10 mL) was slowly added a solution of N-Boc-L-serine (1.55 g, 7.54 mmol) in DMF (5.0 mL) at 0 C. The mixture was stirred at 0 C. for 1 hour. After addition of a solution of <strong>[19064-24-5]1,3-difluoro-2-nitrobenzene</strong> (1.00 g, 6.29 mmol) in DMF (5.0 mL) at 0 C., the reaction mixture was stirred at 0 C. for 4 hours. After quenched with 0.5 M aq. HCl at 0 C., the mixture was extracted with EtOAc, washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hexanes:EtOAc=1:1 to 1:3) to afford (S)-2-(tert-butoxycarbonylamino)-3-(3-fluoro-2-nitrophenoxy)propanoic acid (1.20 g, 55%) as a yellow oil. 1H-NMR (400 MHz, CDCl3): δ 9.38 (1H, brs), 7.40 (1H, q, J=7.6 Hz), 6.87-6.82 (2H, m), 5.54 (1H, d, J=7.6 Hz), 4.73 (1H, d, J=8.4 Hz), 4.58 (1H, dd, J=9.2, 2.4 Hz), 4.41 (1H, dd, J=9.0, 2.6 Hz), 1.45 (9H, s).
 

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