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Chemical Structure| 37763-23-8
Chemical Structure| 37763-23-8
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Product Details of [ 37763-23-8 ]

CAS No. :37763-23-8 MDL No. :MFCD07778088
Formula : C9H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 181.19 Pubchem ID :-
Synonyms :

Safety of [ 37763-23-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 37763-23-8 ]

* 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.

  • Upstream synthesis route of [ 37763-23-8 ]
  • Downstream synthetic route of [ 37763-23-8 ]

[ 37763-23-8 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 37763-23-8 ]
  • [ 22818-40-2 ]
Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
[2] Patent: US2015/112057, 2015, A1, . Location in patent: Paragraph 0062
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  • [ 67-56-1 ]
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 3
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Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
  • 4
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YieldReaction ConditionsOperation in experiment
44% With pyridine; copper(ll) sulfate pentahydrate; acetic acid; Glyoxilic acid In water at 20℃; for 10 h; Step 1:To a solution of (R)-2-amino-2-(4-hydroxyphenyl)acetic acid 25a(D-4Hydroxyphenyl glycine, 10.0 g, 60.1 mmol) in methanol (200 mL) was added dropwise thionyl chloride (8 mL) and stirred at room temperature for 10 h. The reaction mixture was concentrated in vacuum and the residue was washed twice with ether to yield (Pv)-methyl 2-amino-2-(4-hydroxyphenyl)acetate (D-4-hydroxyphenylglycine methyl ester 25b (13.0 g, 60.0 mmol, 100percent) as a white solid. 1H NMR (300 MHz, DMSO- 6) ? 3.68 (s, 3 H), 5.07 (s, 1 H), 6.85 (d, J= 8.5 Hz, 2 H), 7.29 (d, J= 8.6 Hz, 2 H), 9.03 (s, 3 H), 10.02 (s, 1 H). Step 2:(R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate 25b (©-4-hydroxyphenylglycine methyl ester, 0.302 g, 1.39 mmol) was dissolved in a freshly prepared aqueous solution of glyoxylic acid (1.27 g, 13.8 mmol) and copper(II) sulfate pentahydrate (0.35 g, 1.40 mmol) in a buffer containing 2.5 M pyridine and 0.5 M acetic acid. The mixture was stirred for 10 h at room temperature and then extracted with three portions of methylene chloride (10 mL). The organic layers were combined, washed three times with 0.5 M HC1 (20 mL), dried, filtered and concentrated in vacuum to dryness. The residue was purified by flash column chromatography (silica gel, eluting with chloroform) to yield methyl2- (4-hydroxyphenyl)-2-oxoacetate 25c (0.109 g, 6.06 mmol, 44percent) as a clear oil. 1H NMR (300 MHz, CDCls) ? 3.99 (s, 3 H), 5.41 (br s, 1 H), 6.95 (d, J= 8.8 Hz, 2 H), 8.00 (d, J = 8.8 Hz, 2 H).
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3946 - 3952
[2] Patent: WO2013/33093, 2013, A1, . Location in patent: Page/Page column 137; 138
  • 5
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
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  • [ 26531-82-8 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
  • 6
  • [ 67-56-1 ]
  • [ 22818-40-2 ]
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YieldReaction ConditionsOperation in experiment
100% at 20℃; for 10 h; Step 1:To a solution of (R)-2-amino-2-(4-hydroxyphenyl)acetic acid 25a(D-4Hydroxyphenyl glycine, 10.0 g, 60.1 mmol) in methanol (200 mL) was added dropwise thionyl chloride (8 mL) and stirred at room temperature for 10 h. The reaction mixture was concentrated in vacuum and the residue was washed twice with ether to yield (Pv)-methyl 2-amino-2-(4-hydroxyphenyl)acetate (D-4-hydroxyphenylglycine methyl ester 25b (13.0 g, 60.0 mmol, 100percent) as a white solid. 1H NMR (300 MHz, DMSO- 6) ? 3.68 (s, 3 H), 5.07 (s, 1 H), 6.85 (d, J= 8.5 Hz, 2 H), 7.29 (d, J= 8.6 Hz, 2 H), 9.03 (s, 3 H), 10.02 (s, 1 H). Step 2:(R)-methyl 2-amino-2-(4-hydroxyphenyl)acetate 25b (©-4-hydroxyphenylglycine methyl ester, 0.302 g, 1.39 mmol) was dissolved in a freshly prepared aqueous solution of glyoxylic acid (1.27 g, 13.8 mmol) and copper(II) sulfate pentahydrate (0.35 g, 1.40 mmol) in a buffer containing 2.5 M pyridine and 0.5 M acetic acid. The mixture was stirred for 10 h at room temperature and then extracted with three portions of methylene chloride (10 mL). The organic layers were combined, washed three times with 0.5 M HC1 (20 mL), dried, filtered and concentrated in vacuum to dryness. The residue was purified by flash column chromatography (silica gel, eluting with chloroform) to yield methyl2- (4-hydroxyphenyl)-2-oxoacetate 25c (0.109 g, 6.06 mmol, 44percent) as a clear oil. 1H NMR (300 MHz, CDCls) ? 3.99 (s, 3 H), 5.41 (br s, 1 H), 6.95 (d, J= 8.8 Hz, 2 H), 8.00 (d, J = 8.8 Hz, 2 H).
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 18, p. 3946 - 3952
[2] Patent: WO2013/33093, 2013, A1, . Location in patent: Page/Page column 137; 138
[3] Angewandte Chemie - International Edition, 1997, vol. 37, # 19, p. 2708 - 2714
[4] Organic Letters, 2015, vol. 17, # 4, p. 1018 - 1021
[5] Journal of the American Chemical Society, 1978, vol. 100, p. 4555 - 4568
[6] Tetrahedron Asymmetry, 2000, vol. 11, # 8, p. 1789 - 1796
[7] Chemistry - A European Journal, 1999, vol. 5, # 9, p. 2602 - 2621
[8] Journal of the American Chemical Society, 2004, vol. 126, # 14, p. 4490 - 4491
[9] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 19, p. 5161 - 5169
[10] Organic Letters, 2000, vol. 2, # 16, p. 2459 - 2462
[11] Patent: EP1144368, 2004, B1, . Location in patent: Page 78
[12] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 9, p. 3320 - 3334
[13] Patent: WO2011/113486, 2011, A1, . Location in patent: Page/Page column 7-9
[14] Patent: WO2011/161645, 2011, A1, . Location in patent: Page/Page column 23
[15] Patent: WO2013/129879, 2013, A1, . Location in patent: Page/Page column 74
[16] Patent: WO2018/192462, 2018, A1, . Location in patent: Paragraph 295; 296
  • 7
  • [ 67-56-1 ]
  • [ 1327278-14-7 ]
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 8
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Reference: [1] Tetrahedron Asymmetry, 2000, vol. 11, # 8, p. 1789 - 1796
  • 9
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 11
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 13
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Reference: [1] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2022 - 2027
  • 14
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
  • [ 32462-30-9 ]
  • [ 37763-23-8 ]
  • [ 26531-82-8 ]
Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
  • 15
  • [ 43189-12-4 ]
  • [ 22818-40-2 ]
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Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 17, p. 2491 - 2498
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