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[ CAS No. 122709-21-1 ] {[proInfo.proName]}

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Chemical Structure| 122709-21-1
Chemical Structure| 122709-21-1
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Product Details of [ 122709-21-1 ]

CAS No. :122709-21-1 MDL No. :MFCD09878777
Formula : C13H24N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :USINQMZZDNKSQW-VIFPVBQESA-N
M.W : 288.34 Pubchem ID :14961355
Synonyms :

Calculated chemistry of [ 122709-21-1 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.85
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 76.32
TPSA : 68.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.23
Log Po/w (XLOGP3) : 1.06
Log Po/w (WLOGP) : 1.0
Log Po/w (MLOGP) : 0.38
Log Po/w (SILICOS-IT) : -0.03
Consensus Log Po/w : 1.13

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.9
Solubility : 3.63 mg/ml ; 0.0126 mol/l
Class : Very soluble
Log S (Ali) : -2.09
Solubility : 2.37 mg/ml ; 0.00821 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.01
Solubility : 27.9 mg/ml ; 0.0968 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.83

Safety of [ 122709-21-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 122709-21-1 ]

* 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 [ 122709-21-1 ]

[ 122709-21-1 ] Synthesis Path-Downstream   1~39

  • 1
  • [ 122709-21-1 ]
  • [ 102308-32-7 ]
YieldReaction ConditionsOperation in experiment
6.24 g With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 1h;Inert atmosphere; Example 14 Synthesis of tert-Butyl (S)-4-formyl-2,2-dimethyloxazolidine-3-carboxylate (14*) To a solution of Weinreb amide 13* (8.00 g, 27.7 mmol) in THF (100 mL) at 0C were added LiAlH4 (1.0 M in THF, 13.9 mL, 13.9 mmol) dropwise and the solution was stirred for 1 h at 0 C. After 1 h, the solution was cooled to -10 C and KHSO4 (1M, 70 mL) was added carefully and the solution was diluted with Et2O (170 mL). The mixture was allowed to warm to r.t. and stirred for 30 min. The organic layer was separated, dried over MgSO4, filtered and the solvent was removed in vacuo to yield Garner's aldehyde 14* as a pale yellow oil (6.24 g, > 95% purity by 1H NMR). The NMR spectra consist of two sets of signals due to the presence of rotamers. 1H NMR (250 MHz, CDCl3) delta 9.58 (d, J = 0.8 Hz, 1 H), 9.52 (d, J = 2.5 Hz, 1 H), 4.32 (m, 1 H), 4.16 (m, 1 H), 4.06 (m, 4 H), 1.53-1.63 (m, 12 H), 1.49 (s, 9 H), 1.40 (s, 9 H). All spectral data in good accordance with reported data (Synthesis 1998, 1707). The crude product was used in the subsequent reaction without further purification.
6.24 g Example B.2: Synthesis of tert-Butyl (S)-4-formyl-2,2-dimethyloxazolidine-3- carboxylate (14*)To a solution of Weinreb amide 13* (8.00 g, 27.7 mmol) in THF (100 mL) at 0 C were added LiAIH4 (1 .0 M in THF, 13.9 mL, 13.9 mmol) dropwise and the solution was stirred for 1 h at 0 C. After 1 h, the solution was cooled to -10 C and KHSO4 (1 M, 70 mL) was added carefully and the solution was diluted with Et2O (170 mL). The mixture was allowed to warm to r.t. and stirred for 30 min. The organic layer was separated, dried over MgSO4, filtered and the solvent was removed in vacuo to yield Garner's aldehyde 14* as a pale yellow oil (6.24 g, > 95% purity by 1H NMR). The NMR spectra consist of two sets of signals due to the presence of rotamers. 1H NMR (250 MHz, CDCI3) delta 9.58 (d, J = 0.8 Hz, 1 H), 9.52 (d, J = 2.5 Hz, 1 H), 4.32 (m, 1 H), 4.16 (m, 1 H), 4.06 (m, 4 H), 1 .53-1 .63 (m, 12 H), 1 .49 (s, 9 H), 1 .40 (s, 9 H). Allspectral data in good accordance with reported data (Synthesis 1998, 1707). The crude product was used in the subsequent reaction without further purification
With potassium hydrogensulfate; lithium aluminium tetrahydride; In tetrahydrofuran; tert-Butyl (S)-4-formyl-2,2-dimethyloxazolidine-3-carboxylate (4) To a solution of Weinreb amide 3 (8.00 g, 27.7 mmol) in THF (100 mL) at 0 C were added LiAlH4 (1.0 M in THF, 13.9 mL, 13.9 mmol) dropwise and the solution was stirred for 1 h at 0 C. After 1 h, the solution was cooled to -10 C and KHSO4 (1 M, 70 mL) was added carefully and the solution was diluted with Et2O (170 mL). The mixture was allowed to warm to r.t. and stirred for 30 min. The organic layer was separated, dried over MgSO4, filtered and the solvent was removed in vacuo to yield Garner's aldehyde 4 as a pale yellow oil (6.24 g, > 95% purity by 1H NMR). The NMR spectra consist of two sets of signals due to the presence of rotamers. 1H NMR (250 MHz, CDCl3) delta 9.58 (d, J = 0.8 Hz, 1 H), 9.52 (d, J = 2.5 Hz, 1 H), 4.32 (m, 1 H), 4.16 (m, 1 H), 4.06 (m, 4 H), 1.53-1.63 (m, 12 H), 1.49 (s, 9 H), 1.40 (s, 9 H). The crude product was used in the subsequent reaction without further purification.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 1h; 10229] To a solution of Weinreb amide 3 (8.00 g, 27.7 mmol) in THF (100 mE) at 0 C. were added EiA1H4 (1.0 M in THF, 13.9 mE, 13.9 mmol) dropwise and the solution was stirred for 1 h at 0 C. After 1 h, the solution was cooled to-10C. and KHSO4 (1M, 70 mE) was added careffilly and the solution was diluted with Et20 (170 mE). The mixture was allowed to warm to r.t. and stirred for 30 mm. The organic layer was separated, dried over MgSO4, filtered and the solvent was removed in vacuo to yield Gamer?s aldehyde 4 as a pale yellow oil (6.24 g, >95% purity by ?H NMR). The NMR spectra consist of two sets of signals due to the presence of rotamers. ?H NMR (250 MHz, CDC13) oe 9.58 (d, J=0.8 Hz, 1H), 9.52 (d, J=2.5 Hz, 1H), 4.32 (m, 1H), 4.16 (m, 1H), 4.06 (m, 4H), 1.53-1.63 (m, 12H), 1.49 (s, 9H), 1.40 (s, 9H). The crude product was used in the subsequent reaction without thrther purification
(R)-terr-butyl 2,2-dimethyl-4-vinyloxazolidine-3-carboxylate (ICEC0002)[00238] The hydroxamate ICECOOOl (1 g, 3.47 mmol) was dissolved in anhyd. THF(15 mL) and cooled to 00C. 1.0 M LiAlH4 in THF (0.87 mL, 1.73 mmol) was added drop-wise and the mixture was stirred for 30 min. The reaction was then cooled further to -15C and sat. aq. KHSO4 (10 mL) was added carefully, the solution diluted with diethyl ether (25 mL) and stirred vigorously for 30 min. The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo to give the corresponding aldehyde as a pale yellow oil, which was directly used in the next step.

  • 2
  • [ 122709-20-0 ]
  • [ 77-76-9 ]
  • [ 122709-21-1 ]
YieldReaction ConditionsOperation in experiment
96% With boron trifluoride diethyl etherate; In acetone; at 0℃; for 3h; To a cooled (0 C) solution of weinreb?s amide (5.38 g, 22 mmol) and 2,2-dimethoxypropane (80 mL, 130 mmol) in and acetone (25 mL) was slowly dropped a solution of BF3*Et2O (0.3 mL, 2.2 mmol). After stirring for 3 hours, the mixture was quenched with TEA (1 mL) and the resulting mixture was concentrated. The residue was purified by flash chromatography on silica gel (EA/PE = 1/4) to give (S)-tert-butyl4-(methoxy(methyl)carbamoyl)-2,2-dimethyloxazolidine-3-carboxylate (6.0 g, 96%) as a white solid. [alpha]D27 = -37.7 (c 0.84, CHCl3); IR (film):numax 2977, 2937, 1705, 1455, 1391, 1366, 1272, 1248, 1173, 1100, 1064, 999 cm-1; 1H NMR (400 MHz, CDCl3, rotamers) delta 4.80 (dd, J = 7.2, 2.8Hz, 1/2H), 4.73 (dd, J = 7.2, 3.6 Hz, 1/2H), 4.22-4.16 (m, 1H), 3.96 (ddd, J = 16.4, 9.2, 2.8 Hz, 1H), 3.75 (s, 1/2H), 3.70 (s, 1/2H), 3.20 (s, 3H),1.70 (d, J = 10.0 Hz, 3H), 1.55 (d, J = 17.6 Hz 3H), 1.50 (s, 4H), 1.42 (s, 5H) ppm; 13C NMR (100 MHz, CDCl3) delta 171.4, 170.6, 152.2, 151.3,95.0, 94.4, 80.5, 80.0, 66.1, 66.0, 61.2, 57.9, 57.7, 32.6, 32.5, 28.4, 28.3, 25.7, 25.5, 24.7, 24.6 ppm; HRMS (ESI) calcd for [C13H24N2O5+Na+]:311.1583, found: 311.1577.
15.32 g With boron trifluoride diethyl etherate; In acetone; at 20℃; for 1.5h;Inert atmosphere; Example 13 Synthesis of (S)-3-(tert-Butoxycarbonyl)-N-methoxy-2,2, N-trimethyloxazolidine-4-carboxamide (13*) To a solution of L-Boc-serine (12.33 g, 60.1 mmol) in DCM (240 mL) were added N,O-dimethylhydroxylamine hydrochloride (6.04 g, 61.9 mmol) and N-methylmorpholine (6.8 mL, 61.9 mmol) at 0 C. To this solution was added N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (11.86 g, 61.9 mmol) portionwise over a period of 20 min. and the solution was stirred for another 1 h. Then, aqueous HCl solution (1.0 M, 30 mL) was added and the aqueous layer was extracted with CH2Cl2 (2 x 100 mL). The combined organic layers were washed with saturated aqueous NaHCO3 solution (30 mL) and the aqueous layer was again extracted with CH2Cl2 (100 mL). The combined organic layers were dried over MgSO4 and the solvent was removed in vacuo to obtain the corresponding Weinreb amide (14.07 g, 94%) as white solid. Rf = 0.3 (EtOAc); 1H NMR (250 MHz, CDCl3) delta 5.60 (d, J = 6.0 Hz, 1 H), 4.77 (br s, 1 H), 1.42 (s, 9 H), 3.80 (d, J = 3.3 Hz, 2 H), 3.76 (s, 3 H), 3.21 (s, 3 H), 2.66 (br s, 1 H). The crude product was dissolved in acetone (180 mL) to which 2,2-dimethoxypropane (57 mL) and BF3·Et2O (0.5 mL) were added. The orange solution was stirred for 90 min. at r.t. and then quenched with Et3N (1.2 mL) and solvents removed in vacuo. The crude product was purified by flash column chromatography on silica gel (gradient EtOAc/cyclohexane = 1:2 ? 1:1) to yield isopropylidene-protected Weinreb amide 13* (15.32 g, 89% over two steps) as a white solid. The NMR spectra consist of two sets of signals due to the presence of rotamers. [alpha]Dr.t. = -30.9 (c = 1, CHCl3); Rf = 0.45 (Hexanes/EtOAc = 1:1); IR (film) numax 2976, 2938, 1702, 1682, 1364, 1167, 1098, 998, 848, 768, 716; 1H NMR (250 MHz, CDCl3) delta 4.77 (dd, J = 9.8, 2.8 Hz, 1 H), 4.70 (dd, 7.5, 3.8, Hz, 1 H), 4.18 (dd, J = 7.5, 4.0 Hz, 1 H), 4.15 (dd, J = 7.8, 3.8 Hz, 1 H), 3.95 (dd, J = 9.3, 3.0 Hz, 1 H), 3.91 (dd, J = 9.0, 3.5 Hz), 3.72 (s, 3 H), 3.68 (s, 3 H), 3.19 (s, 6 H), 1.68 (s, 3 H), 1.66 (s, 3 H), 1.54 (s, 3 H), 1.50 (s, 3 H), 1.47 (s, 9 H), 1.39 (s, 9 H); 13C NMR (101 MHz, CDCl3) delta 171.4, 170.7, 152.2, 151.4, 95.1, 94.5, 80.6, 80.0, 66.2, 66.0, 61.3, 61.3, 57.9, 57.8, 28.5, 28.4, 25.8, 25.5, 24.8, 24.6; HR ESI Calcd for C13H24N2O5 [M+Na+]: 311.1577 found: 311.1582.
With boron trifluoride diethyl etherate; In acetone; at 20℃; for 1.5h;Inert atmosphere; Example B.1 : Synthesis of (S)-3-(tert-Butoxycarbonyl)-N-methoxy-2,2, N- trimethyloxazolidine-4-carboxamide (13*)The crude product was dissolved in acetone (180 mL) to which 2,2- dimethoxypropane (57 mL) and BF3 Et2O (0.5 mL) were added. The orange solution was stirred for 90 min. at r.t. and then quenched with Et3N (1 .2 mL) and solvents removed in vacuo. The crude product was purified by flash column chromatography on silica gel (gradient EtOAc/cyclohexane = 1 :2 - 1 :1 ) to yield isopropylidene- protected Weinreb amide 13* (15.32 g, 89% over two steps) as a white solid. The NMR spectra consist of two sets of signals due to the presence of rotamers. [a]Dr t = -30.9 (c = 1 , CHCI3); Rf = 0.45 (Hexanes/EtOAc = 1 :1 ); IR (film) vmax 2976, 2938, 1702, 1682, 1364, 1 167, 1098, 998, 848, 768, 716; 1H NMR (250 MHz, CDCI3) delta 4.77 (dd, J = 9.8, 2.8 Hz, 1 H), 4.70 (dd, 7.5, 3.8, Hz, 1 H), 4.18 (dd, J = 7.5, 4.0 Hz, 1 H), 4.15 (dd, J = 7.8, 3.8 Hz, 1 H), 3.95 (dd, J = 9.3, 3.0 Hz, 1 H), 3.91 (dd, J = 9.0, 3.5 Hz), 3.72 (s, 3 H), 3.68 (s, 3 H), 3.19 (s, 6 H), 1 .68 (s, 3 H), 1 .66 (s, 3 H), 1 .54 (s, 3 H), 1 .50 (s, 3 H), 1 .47 (s, 9 H), 1 .39 (s, 9 H); 13C NMR (101 MHz, CDCl3) delta 171 .4, 170.7, 152.2, 151 .4, 95.1 , 94.5, 80.6, 80.0, 66.2, 66.0, 61 .3, 61 .3, 57.9, 57.8, 28.5, 28.4, 25.8, 25.5, 24.8, 24.6; HR ESI Calcd for Ci3H24N2O5 [M+Na+]: 31 1 .1577 found: 31 1 .1582.
15.32 g With boron trifluoride diethyl etherate; In acetone; at 20℃; for 1.5h; To a solution of L-l3oc-serine 2 (12.33 g, 60.1 mmol) in CH2C12 (240 mE) were added N,O-dimethylhydroxylamine hydrochloride (6.04 g, 61.9 mmol) and N-methylmorpholine (6.8 mE, 61.9 mmol) at 0C. To this solution was added N-(3-dimethylaminopropyl)-N?-ethylcarbodiim- ide hydrochloride (11.86 g, 61.9 mmol) portionwise over a period of 20 mi and the solution was stirred for another 1 h. Then, aq. HC1 solution (1.0 M, 30 mE) was added and the aqueous layer was extracted with CH2C12 (2x100 mE). The combined organic layers were washed with sat. aq. NaHCO3 solution (30 mE) and the aqueous layer was again extracted with CH2C12 (100 mE). The combined organic layers were dried over MgSO4 and the solvent was removed in vacuo to obtain the corresponding Weinreb amide (14.07 g, 94%) as white solid. R1=0.3 (EtOAc); ?H NMR (250 MHz, CDC13) oe 5.60 (d, J=6.0 Hz, 1H), 4.77 (br s, 1H), 1.42 (s, 9H), 3.80 (d, J=3.3 Hz, 2H), 3.76 (s, 3H), 3.21 (s, 3H), 2.66 (br s, 1H). The crude product was dissolved in acetone (180 mE) to which 2,2-dimethoxypropane (57 mE) and 13F3Et2O (0.5 mE) were added. The orange solution was stirred for 90 mm. at tt. and then quenched with Et3N (1.2 mE) and solvents removed in vacuo. The crude product was purified by flash column chromatography on silica gel (gradient EtOAc/cyclohexane=1:2- 1:1) to yield isopropylidene-protected Weinreb amide 3 (15.32 g, 89% over two steps) as a white solid. The NMR spectra consist of two sets of signals due to the presence of rotamers. [a]D?t=-30.9 (c=1, CHC13); R1=0.45 (Hexanes/ EtOAc=1:1); IR (film) Vmax 2976, 2938, 1702, 1682, 1364, 1167, 1098, 998, 848, 768,716; ?H NMR (250 MHz, CDC13) oe 4.77 (dd, J=9.8, 2.8 Hz, 1H), 4.70 (dd, 7.5, 3.8, Hz, 1H), 4.18 (dd, J=7.5, 4.0 Hz, 1H), 4.15 (dd, J=7.8, 3.8 Hz, 1H), 3.95 (dd, J=9.3, 3.0 Hz, 1H), 3.91 (dd, J=9.0, 3.5 Hz), 3.72 (s,3H), 3.68 (s, 3H), 3.19 (s, 6H), 1.68 (s, 3H), 1.66 (s, 3H), 1.54(s,3H), 1.50(s,3H), 1.47(s, 9H), 1.39(s, 9H); ?3CNMR(101MHz, CDC13) oe 171.4, 170.7, 152.2, 151.4, 95.1, 94.5, 80.6,80.0, 66.2, 66.0, 61.3, 61.3, 57.9, 57.8, 28.5,28.4,25.8,25.5,24.8, 24.6; HR ESI Calcd for C,3H24N205 [M+Na]: 311.1577. found: 311.1582.
The solid was dissolved in acetone (500 mL) and 2,2-dimethoxypropane (200 mL) and BF3OEt2 (1.6 mL) were added until there was a permanent change in colour (colourless to dark yellow) and the reaction was stirred for 90 min. Et3N (4 mL) was added to quench the reaction and the solvent was evaporated to give a solid which was purified by column chromatography on silica (ethyl acetate:hexanes = 1 :4). The product ICECOOOl was obtained as a white solid (48.20 g, 87% over three steps).[00237] M.p. 63-64C (ethyl acetate). [alpha]D (c 2.36, CHCl3) -36.1. 1H NMR (CDCl3,300 MHz) delta 4.73 (m, IH), 4.15 (m, IH), 3.92 (m, IH), 3.70 (m, 3H), 3.19 (s, 3H), 1.66 (m, 3H), 1.54-1.39 (m, 12H). 13C NMR (CDCl3, 75 MHz) delta 171.2, 170.5, 152.1, 151.2, 94.9, 94.3, 80.5, 79.9, 66.1, 65.8, 61.1, 57.8, 57.6, 32.5, 32.4, 28.3, 25.6, 25.3, 24.6, 24.5.

  • 3
  • [ 7103-09-5 ]
  • [ 122709-21-1 ]
  • [ 183603-95-4 ]
  • 4
  • [ 19578-68-8 ]
  • [ 122709-21-1 ]
  • [ 488835-85-4 ]
YieldReaction ConditionsOperation in experiment
With magnesium; In diethyl ether; at 25℃; The synthesis of ketone derivatives:39a-b is outlmed m acnemc 11. Serine was converted in three steps into Weinreb's hydroxamate 36; whose condensation with the Grignard reagent 4-benzyloxyphenyl magnesium iodide proceeded to give the expected ketone 37 in modest yield. TFA deprotection afforded the ammonium salt 38, which underwent selective acylation followed by phosphorylation. TFA deprotection provided ketones 39a-b.
  • 7
  • [ 122709-21-1 ]
  • [ 149180-94-9 ]
  • 8
  • [ 122709-21-1 ]
  • [ 183603-94-3 ]
  • 9
  • [ 122709-21-1 ]
  • tert-butyl (4S,1'S)-2,2-dimethyl-4-(1'-hydroxy-4'-pentenyl)oxazolidine-3-carboxylate [ No CAS ]
  • 10
  • [ 122709-21-1 ]
  • [ 336625-39-9 ]
  • 11
  • [ 122709-21-1 ]
  • [ 336625-45-7 ]
  • 12
  • [ 122709-21-1 ]
  • [ 336625-40-2 ]
  • 13
  • [ 122709-21-1 ]
  • [ 336625-41-3 ]
  • 14
  • [ 122709-21-1 ]
  • [ 336625-42-4 ]
  • 15
  • [ 122709-21-1 ]
  • [ 336625-43-5 ]
  • 16
  • [ 122709-21-1 ]
  • [ 142632-81-3 ]
  • 17
  • [ 122709-21-1 ]
  • [ 142632-82-4 ]
  • 18
  • [ 122709-21-1 ]
  • [ 142632-80-2 ]
  • 19
  • [ 122709-21-1 ]
  • [ 142573-63-5 ]
  • 20
  • [ 122709-21-1 ]
  • [ 142573-62-4 ]
  • 21
  • [ 122709-21-1 ]
  • [ 142573-64-6 ]
  • 22
  • [ 122709-21-1 ]
  • [ 142573-61-3 ]
  • 24
  • [ 75-16-1 ]
  • [ 122709-21-1 ]
  • [ 785828-28-6 ]
YieldReaction ConditionsOperation in experiment
82% In tetrahydrofuran; at 0℃; for 3h; To a cooled (0 C) solution of <strong>[122709-21-1](S)-<strong>[122709-21-1]tert-butyl 4-(methoxy(methyl)carbamoyl)-2,2-dimethyloxazolidine-3-carboxylate</strong></strong> (5.8 g, 20.1 mmol) in THF (50 mL) was slowly dropped a solution of CH3MgBr (2.8 M in THF, 60.3 mmol, 21.5 mL) and stirred for 3 hours. Then the mixture wasquenched with a saturated NH4Cl aqueous solution and extracted with EtOAc (100 mL × 2). The combined organic layers were washed with brine (50 mL × 2) and dried over anhydrous MgSO4. Filtered and concentrated, the residue was purified by flash chromatography on silica gel(EA/PE = 1/10) to give ketone (4.0 g, 82%) as a colorless oil. [alpha]D27 = -56.0 (c 0.92, CHCl3); IR (film): numax 2978, 2934, 1706, 1478, 1457, 1391,1378, 1366, 1271, 1248, 1211, 1175, 1090, 1057; 1H NMR (400 MHz, CDCl3, rotamers ) delta 4.41 (dd, J = 7.2, 2.8 Hz, 2/5H), 4.28 (dd, J = 7.6, 2.8Hz, 3/5H), 4.18-4.10 (m, 1H), 3.98 (dd, J = 9.2, 2.4 Hz, 2/5H), 3.93 (dd, J = 9.2, 2.8 Hz, 3/5H), 2.22 (s, 2/5H), 2.20 (s, 3/5H), 1.71-1.65 (m, 3H),1.54-1.42 (m, 12H) ppm; 13C NMR (100 MHz, CDCl3) delta 207.0, 206.5, 152.5, 151.4, 4, 95.2, 94.5, 81.0, 80.7, 65.7, 65.6, 65.5, 65.2, 28.3, 28.2,26.5, 26.3, 26.0, 25.5, 24.8, 23.7 ppm; HRMS (ESI) calcd for [C12H21NO4+Na+]: 266.1368, found: 266.1358.
  • 25
  • [ 90965-06-3 ]
  • [ 122709-21-1 ]
  • [ 162107-48-4 ]
  • 26
  • [ 122709-21-1 ]
  • (R)-4-((Z)-2-ethoxycarbonyl-1-methyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]
  • [ 1168208-13-6 ]
  • 27
  • [ 3262-72-4 ]
  • [ 6638-79-5 ]
  • [ 25952-53-8 ]
  • [ 122709-21-1 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; In dichloromethane; (S)-3-(tert-Butoxycarbonyl)-N-methoxy-2,2,N-trimethyloxazolidine-4-carboxamide (3) To a solution of L-Boc-serine 2 (12.33 g, 60.1 mmol) in CH2Cl2 (240 mL) were added N,O-dimethylhydroxylamine hydrochloride (6.04 g, 61.9 mmol) and N-methylmorpholine (6.8 mL, 61.9 mmol) at 0 C. To this solution was added N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (11.86 g, 61.9 mmol) portionwise over a period of 20 min. and the solution was stirred for another 1 h. Then, aq. HCl solution (1.0 M, 30 mL) was added and the aqueous layer was extracted with CH2Cl2 (2 x 100 mL). The combined organic layers were washed with sat. aq. NaHCO3 solution (30 mL) and the aqueous layer was again extracted with CH2Cl2 (100 mL). The combined organic layers were dried over MgSO4 and the solvent was removed in vacuo to obtain the corresponding Weinreb amide (14.07 g, 94%) as white solid. Rf = 0.3 (EtOAc); 1H NMR (250 MHz, CDCl3) delta 5.60 (d, J = 6.0 Hz, 1 H), 4.77 (br s, 1 H), 1.42 (s, 9 H), 3.80 (d, J = 3.3 Hz, 2 H), 3.76 (s, 3 H), 3.21 (s, 3 H), 2.66 (br s, 1 H). The crude product was dissolved in acetone (180 mL) to which 2,2-dimethoxypropane (57 mL) and BF3·Et2O (0.5 mL) were added. The orange solution was stirred for 90 min. at r.t. and then quenched with Et3N (1.2 mL) and solvents removed in vacuo. The crude product was purified by flash column chromatography on silica gel (gradient EtOAc/cyclohexane = 1:2 ? 1:1) to yield isopropylidene-protected Weinreb amide 3 (15.32 g, 89% over two steps) as a white solid.
  • 28
  • [ 122709-21-1 ]
  • [ 214556-58-8 ]
  • 31
  • [ 122709-21-1 ]
  • (4R,1'Z)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-(1'-hexadecenyl)oxazolidine [ No CAS ]
  • 32
  • [ 122709-21-1 ]
  • [ 214556-58-8 ]
  • [ 214556-60-2 ]
  • 33
  • [ 122709-20-0 ]
  • [ 77-76-9 ]
  • [ 67-64-1 ]
  • [ 122709-21-1 ]
  • 34
  • [ 122709-21-1 ]
  • (R)-4-[2-(diethoxyphosphoryl)vinyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]
  • tert-butyl 4-(2-(diethoxyphosphoryl)vinyl)-2,2-dimethyloxazolidine-3-carboxylate [ No CAS ]
  • 35
  • [ 122709-21-1 ]
  • [ 1092444-41-1 ]
  • [ 1092444-40-0 ]
  • 36
  • [ 59524-02-6 ]
  • [ 122709-21-1 ]
  • 37
  • [ 122709-21-1 ]
  • C27H36NO6P [ No CAS ]
  • 38
  • [ 122709-21-1 ]
  • [ 352-13-6 ]
  • tert-butyl (4S)-4-(4-fluorobenzoyl)-2,2-dimethyl-oxazolidine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% In tetrahydrofuran; diethyl ether; at 0 - 20℃; for 2h;Inert atmosphere; Cooling with ice; M 4-fluorophenylmagnesium bromide (26.1 mmol, 13.1 mL) in Et20 was added slowly to a solution of tert-butyl (4S)-4-[methoxy(methyl)carbamoyl]-2,2-dimethyl-oxazolidine-3- carboxylate (23.8 mmol, 6.85 g, Tetrahedron Letters (2014), 6903-6906) in dry THF (80 ml.) at 0-5 C under argon. The ice-bath was removed and the mixture was warmed to rt and stirred for 2 hours. LCMS showed full conversion. Quenched with 10% NH4CI (50 ml_), extracted with Et20 (2 x 50 ml_), dried (Na2S04) and evaporated to an orange oil. Chromatographed on silica using EtOAc: heptane as eluent. Intermediate 11 (3.10 g) was isolated as a white crystals in 40% yield. ^NMR showed BOC rotamers in a 4: 5 ratio. UPLC-MS : tR = 0.84 (M + H+) = 224.2 (loss of BOC)NMR (300 MHz, Chloroform-d) delta 8.00 - 7.92 (m, 2H), 7.22 - 7.10 (m, 2H), 5.42 (dd, J = 7.4, 3.0 Hz, 0.44H, a-H), 5.36 - 5.30 (m, 0.56H, a-H), 4.30 (td, J = 8.5, 3.9 Hz, 1H), 3.93 (ddd, J = 8.9, 5.4, 3.3 Hz, 1H), 1.74 (d, J = 10.8 Hz, 2H), 1.59 (d, J = 11.1 Hz, 2H), 1.50 (s, 4H, BOC), 1.28 (s, 5H, BOC).
  • 39
  • [ 122709-21-1 ]
  • [ 352-13-6 ]
  • C17H24FNO4 [ No CAS ]
  • C17H24FNO4 [ No CAS ]
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