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[ CAS No. 1145-80-8 ]

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Chemical Structure| 1145-80-8
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CAS No. :1145-80-8 MDL No. :MFCD00002662
Formula : C11H13NO5 Boiling Point : 487.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :239.22 g/mol Pubchem ID :100310
Synonyms :

Safety of [ 1145-80-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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  • Upstream synthesis route of [ 1145-80-8 ]
  • Downstream synthetic route of [ 1145-80-8 ]

[ 1145-80-8 ] Synthesis Path-Upstream   1~23

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Reference: [1] Tetrahedron, 2000, vol. 56, # 22, p. 3625 - 3633
[2] Journal of the American Chemical Society, 1966, vol. 88, p. 2304 - 2309
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Reference: [1] Tetrahedron, 2000, vol. 56, # 22, p. 3625 - 3633
  • 3
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  • [ 77987-49-6 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 17, p. 5479 - 5486
  • 4
  • [ 2768-56-1 ]
  • [ 6081-61-4 ]
  • [ 1145-80-8 ]
Reference: [1] Chemistry Letters, 1988, p. 1125 - 1128
  • 5
  • [ 1145-80-8 ]
  • [ 100-39-0 ]
  • [ 21209-51-8 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253
[2] Tetrahedron Asymmetry, 2007, vol. 18, # 18, p. 2121 - 2124
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1343 - 1350
[4] Amino Acids, 2010, vol. 39, # 2, p. 367 - 373
[5] Tetrahedron Letters, 1968, p. 6323 - 6326
[6] Synthesis, 1979, p. 957 - 961
  • 6
  • [ 1145-80-8 ]
  • [ 2978-10-1 ]
  • [ 21209-51-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 17, p. 2907 - 2915
  • 7
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  • [ 21209-51-8 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 2166,2168
  • 8
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  • [ 100-44-7 ]
  • [ 21209-51-8 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 1, p. 87 - 93
  • 9
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  • [ 104-15-4 ]
  • [ 100-51-6 ]
  • [ 21209-51-8 ]
Reference: [1] Journal of the Chemical Society, 1959, p. 941,945
[2] Acta Chemica Scandinavica (1947-1973), 1957, vol. 11, p. 1232,1235
  • 10
  • [ 2016-04-8 ]
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Reference: [1] Collection of Czechoslovak Chemical Communications, 1974, vol. 39, p. 634 - 646
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  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h; Adapting the procedure of Chhabra et al.,4 to aflame-dried 250 mL round bottom flask containing Cbz-Serine-OH 8 (12.0 g, 50.0 mmol, 1.00 equiv) and K2CO3(7.60 g, 55.0 mmol, 1.10 equiv) in DMF (85 mL, 0.60 M) at 0 °C was added methyl iodide (6.20 mL, 100 mmol,2.00 equiv) over 30 minutes. The reaction was allowed to warm slowly to room temperature and stirred overnightThe reaction mixture was diluted with EtOAc (500 mL) and washed with a 1:4 mixture of saturated aqueousNaCl:H2O (2 x 100 mL). The combined aqueous washes were back extracted with EtOAc (2 x 150 mL). Thecombined organic extracts were washed sequentially with H2O (2 x 200 mL), saturated aqueous NaCl (2 x 200 mL),5percent aqueous (w/v) LiCl (2 x 200 mL), and again saturated aqueous NaCl (1 x 200 mL). The combined aqueouswashes were further back-extracted with Et2O (1 x 200 mL), and the combined organics were dried over Na2SO4,filtered, and concentrated in vacuo to afford the title compound as a viscous, colorless oil (13.0 g, 99percent) that wasused without further purification (Note: The crude material contained residual DMF). TLC: Rf = 0.17 (40percentEtOAc/hexanes; UV/KMnO4); 1H NMR (600 MHz, CDCl3) δ 7.40–7.30 (m, 5H), 5.79–5.49 (m, 1H), 5.13 (s, 2H),4.50–4.40 (m, 1H), 4.05–3.98 (m, 1H), 3.96–3.90 (m, 1H), 3.79 (s, 3H), 2.07 (t, J = 6.2 Hz, 1H); 13C NMR (151MHz, CDCl3) δ 171.0, 156.3, 136.2, 128.7, 128.4, 128.3, 67.4, 63.6, 56.2, 53.0. The spectra were in close agreementwith the literature.4 IR (FT-ATR, neat, cm-1): 3362, 2654, 1699, 1519, 1454, 1438, 1209, 1057, 976, 911, 750, 697;HRMS (ESI) m/z for [M+Na]+ C12H15NO5Na requires 276.0848, observed 276.0850; [α]D20 +8.3 (c = 1.0, CHCl3).
50% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; General procedure: A solution of N-benzyloxycarbonyl-L-amino acid S5 (7.9 mmol) in DMF (20 ml) was added methyliodide (1.1 g, 7.9 mmol) and potassium carbonate (1.2 g, 8.7 mmol). The reaction mixture waskept at room temperature for 3 hours. The methylated products were purified by column chromatographyin the yields of 50percent (1.0 g, colorless-oil) for serine and 92percent (1.9 g, white-solid) for threonine.The methylated amino acid (4.0 mmol) in DMF (10 ml) was mixed with TBDPSCl (2.2 g, 7.9mmol), imidazole (810 mg, 11.9 mmol) and catalytic amount of DMAP. The reaction was processedat 45 °C for 7 hours. The desired products were purified by column chromatography in theyields of 90percent (1.7 g, colorless-oil) for serine and 90percent (1.8 g, white-solid) for threonine. The silylproduct (500 mg, 1.0 mmol) in DMF (1 ml) was reacted with 15percent NaOH (5 ml) for 2 hours. Thereaction mixture was quenching by 1 N HCl(aq) and 6 was extracted by ethyl acetate. The desiredamino acid 6 was obtained after removal of ethyl acetate in the quantitative yields (470 mg,white-solid for serine; 486 mg, colorless-oil for threonine).
Reference: [1] Chemistry Letters, 2001, # 2, p. 102 - 103
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 20, p. 4871 - 4874
[3] Journal of Organic Chemistry, 1985, vol. 50, # 8, p. 1264 - 1271
[4] Journal of Organic Chemistry, 2002, vol. 67, # 12, p. 4017 - 4029
[5] Journal of Organic Chemistry, 1999, vol. 64, # 2, p. 498 - 506
[6] Synlett, 2018, vol. 29, # 11, p. 1430 - 1436
[7] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 7, p. 1160 - 1164
[8] Journal of Organic Chemistry, 2013, vol. 78, # 21, p. 10853 - 10859
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YieldReaction ConditionsOperation in experiment
16.8 g at 0 - 20℃; Inert atmosphere To a slurry of L-serine (10.5 g, 100 mmol) in H2O (100 mL), NaHCO3 (21.0 g, 250 mmol), and THF (50 mL) were added successively at 0 °C with cooling of the reaction vessel in an ice-water bath. The mixture was stirred for 30 min, benzyl chloroformate (15.5 mL, 110 mmol) was added dropwise at 0 °C. The ice-water bath was then removed, and the mixture was stirred for 4 h at r.t. The resulting mixture was washed with Et2O (2 × 50 mL) and acidified to pH 2 with aq 3 M HCl. The obtained solution was extractedwith EtOAc (1 × 100 mL and 3 × 50 mL). The combined organicphase was washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was dissolved in MeOH (150 mL), and SOCl2 (8.5 mL, 117 mmol) was then added dropwise to the solution at 0 °C under an N2 atmosphere. The mixture wasstirred for 10 min at 0 °C, the ice-water bath was then removed, and the mixture was stirred overnight at r.t. The resulting solution wasthen concentrated under reduced pressure, dissolved in Et2O (150mL), washed with cold sat. NaHCO3, dried (Na2SO4), filtered, and concentrated under reduced pressure. The obtained crude material was purified by column chromatography (silica gel, hexane–EtOAc, 1:1 to 1:3) to give the product (16.8 g, 66 mmol, 66percent, 2 steps).
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 11, p. 3188 - 3191
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 23, p. 3397 - 3410
[4] Journal of Organic Chemistry, 1996, vol. 61, # 2, p. 581 - 586
[5] Organic Letters, 2005, vol. 7, # 22, p. 5047 - 5050
[6] Tetrahedron, 2007, vol. 63, # 35, p. 8645 - 8657
[7] Chemical Communications, 2014, vol. 50, # 88, p. 13608 - 13611
[8] Journal of Organic Chemistry, 1985, vol. 50, # 8, p. 1264 - 1271
[9] European Journal of Organic Chemistry, 2001, # 16, p. 3067 - 3074
[10] Chemical Communications, 2005, # 2, p. 168 - 170
[11] Bulletin of the Chemical Society of Japan, 1978, vol. 51, # 6, p. 1897 - 1898
[12] Synthesis, 1995, # 9, p. 1155 - 1158
[13] Journal of Organic Chemistry, 2004, vol. 69, # 10, p. 3590 - 3592
[14] Synthesis (Germany), 2014, vol. 46, # 10, p. 1367 - 1373
  • 13
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Reference: [1] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 1, p. 87 - 93
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 923 - 928
[3] Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713
[4] Journal of Organic Chemistry, 1985, vol. 50, # 8, p. 1264 - 1271
[5] Canadian Journal of Chemistry, 1956, vol. 34, p. 1182,1184
[6] Collection of Czechoslovak Chemical Communications, 1965, vol. 30, p. 1611,1615
[7] Helvetica chimica acta, 1975, vol. 58, # 5, p. 1471 - 1477
[8] Tetrahedron Letters, 1988, vol. 29, # 17, p. 2019 - 2022
[9] Journal of the Chemical Society, Chemical Communications, 1995, # 10, p. 1061 - 1062
[10] Tetrahedron, 1999, vol. 55, # 51, p. 14769 - 14776
  • 14
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  • [ 77-78-1 ]
  • [ 1676-81-9 ]
Reference: [1] Patent: US4622417, 1986, A,
  • 15
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  • [ 100-39-0 ]
  • [ 20806-43-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 9, p. 2699 - 2706
[2] European Journal of Medicinal Chemistry, 1998, vol. 33, # 7-8, p. 635 - 645
  • 16
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  • [ 20806-43-3 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 10, p. 1939 - 1944
  • 17
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  • [ 59524-07-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 17, p. 2907 - 2915
  • 18
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  • [ 84713-20-2 ]
Reference: [1] Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713
  • 19
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  • [ 19647-68-8 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 7, p. 3702 - 3709
  • 20
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  • [ 19647-68-8 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 7, p. 1160 - 1164
  • 21
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  • [ 26054-60-4 ]
YieldReaction ConditionsOperation in experiment
72% With dimethyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; acetonitrile at -55℃; for 2 h; Inert atmosphere Example 4; Standard Procedure for the Synthesis of Ddz-Dap(Boc-Me)-OH (Ddz-AA4, FIG. 2); Step 4-1. Z-Serine-β-lactone (AA4-2).; This intermediate was prepared in an analogous fashion to that described previously for the Boc derivative AA3-1. In a dry 250 mL 3-neck flask equipped with a mechanical stirrer under nitrogen atmosphere was added triphenylphosphine (4.5 g, 17.1 mmol, 1.1 eq.), followed by 100 mL of an anhydrous THF:CH3CN (1:9) solvent mixture. The mixture was stirred until a solution was obtained and then cooled to -55° C. (bath temperature) and dimethylazodicarboxylate (DMAD, 1.9 mL, 17.1 mmol, 1.1 eq) was added dropwise over 10 min. After completion of the addition, the mixture was stirred for 20 min, then a solution of Z-Ser-OH (AA4-1, 3.7 g, 15.5 mmol, 1.0 eq) in 50 mL of anhydrous THF:CH3CN (1:9) was added dropwise over 30 min. The reaction mixture was stirred at -55° C. for 1.5 h, then the cooling bath removed and the solution allowed to warm slowly to room temperature. Once the mixture reached room temperature, the solvent was evaporated under reduced pressure. The resulting yellow oil was purified by flash chromatography [gradient, hexanes/EtOAc, (80:20) to (60:40)] to give 2.5 g of AA4-2 as a white solid in 72percent yield. Purification of the crude oil is preferentially performed the same day to avoid decomposition. DCM can be added to help solubilize the residue.TLC (hexanes/EtOAc (60/40): Rf=0.55 (UV, CMA)
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 22, p. 2643 - 2646
[2] Patent: US2010/93720, 2010, A1, . Location in patent: Page/Page column 38
[3] Journal of the American Chemical Society, 1985, vol. 107, # 24, p. 7105 - 7109
[4] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3240 - 3243
[5] Organic Syntheses, 1992, vol. 70, p. 1 - 1
[6] Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713
[7] Canadian Journal of Chemistry, 1986, vol. 64, p. 706 - 713
[8] Synthetic Communications, 1995, vol. 25, # 16, p. 2475 - 2482
[9] Journal of Medicinal Chemistry, 1997, vol. 40, # 24, p. 3979 - 3985
[10] Journal of Organic Chemistry, 2002, vol. 67, # 5, p. 1536 - 1547
[11] Chemistry Letters, 1982, p. 45 - 48
[12] Patent: US2010/22605, 2010, A1, . Location in patent: Page/Page column 49-50
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  • [ 1972-28-7 ]
  • [ 26054-60-4 ]
YieldReaction ConditionsOperation in experiment
45% With triphenylphosphine In acetonitrile a
L-2-Amino-3-phenylaminoethylpropionic Acid
54.8 g (0.209 mol) of triphenylphosphine were suspended in 600 ml of acetonitrile and, with exclusion of moisture, cooled to -35° C. to -45° C.
At this temperature, 36.4 g (0.209 mol) of diethyl azodicarboxylate were then added dropwise over a period of 50 min.
The mixture was stirred at -35° C. for another 15 min.
A solution of 50 g (0.209 mol) of N-benzyloxycarbonyl-L-serine in 500 ml of acetonitrile was added dropwise to this mixture, the temperature being kept below -35° C.
The mixture was then allowed to react at 5° C. for another 12 h and warmed to RT.
The reaction solution was freed from solvent under reduced pressure and the crude product was purified by medium pressure chromatography over silica gel (DCM/AcCN: 25/1).
Removal of the solvent gave 20.8 g (yield 45percent) of pure N-benzyloxy-carbonyl-L-serine-β-lactone (see also Org. Synth. 1991 (70) 1ff.) in fine needles.
Empirical formula C11H11NO4; M.W.=221.2; MS (M+H) 222.1.
Reference: [1] Patent: US2003/119820, 2003, A1,
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Reference: [1] Patent: WO2004/22553, 2004, A1, . Location in patent: Page/Page column 12-13
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