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[ CAS No. 83793-44-6 ] {[proInfo.proName]}

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Chemical Structure| 83793-44-6
Chemical Structure| 83793-44-6
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Product Details of [ 83793-44-6 ]

CAS No. :83793-44-6 MDL No. :MFCD00600893
Formula : C18H19NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 313.35 Pubchem ID :-
Synonyms :

Safety of [ 83793-44-6 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 83793-44-6 ]

* 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 [ 83793-44-6 ]

[ 83793-44-6 ] Synthesis Path-Downstream   1~79

  • 1
  • [ 6066-82-6 ]
  • [ 83793-44-6 ]
  • [ 146765-85-7 ]
Reference： [1]Journal of Pharmaceutical Sciences,1993,vol. 82,p. 1 - 10
  • 2
  • [ 83793-44-6 ]
  • [ 6638-79-5 ]
  • [ 205983-74-0 ]
Reference： [1]Organic Process Research and Development,1998,vol. 2,p. 186 - 193
[2]Tetrahedron Letters,1994,vol. 35,p. 3745 - 3746
  • 3
  • [ 83793-44-6 ]
  • methyl 2-amino-3-cyclohexyl-3-oxopropioate hydrochloride [ No CAS ]
  • 2-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-3-cyclohexyl-3-oxo-propionic acid methyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 211 - 214
  • 4
  • [ 83793-44-6 ]
  • [ 543-27-1 ]
  • C23H27NO6 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 5
  • [ 771-61-9 ]
  • [ 83793-44-6 ]
  • Z-Hph-OPfp [ No CAS ]
Reference： [1]Journal fur Praktische Chemie - Chemiker-Zeitung,1994,vol. 336,p. 525 - 529
  • 6
  • [ 83793-44-6 ]
  • (2S,3S)-3-amino-2-hydroxypentanoyl-D-leucyl-L-valine t-butyl ester [ No CAS ]
  • [ 1062494-29-4 ]
Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 890 - 899
  • 7
  • [ 83793-44-6 ]
  • (R)-2-((S)-2-Hydroxy-2-pyrrolidin-2-yl-acetylamino)-4-methyl-pentanoic acid tert-butyl ester [ No CAS ]
  • (R)-2-{2-[(S)-1-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyryl)-pyrrolidin-2-yl]-2-hydroxy-acetylamino}-4-methyl-pentanoic acid tert-butyl ester [ No CAS ]
Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 900 - 908
  • 8
  • [ 288068-80-4 ]
  • [ 83793-44-6 ]
Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 890 - 899
  • 9
  • [ 51-67-2 ]
  • [ 83793-44-6 ]
  • [ 1026554-56-2 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 10
  • [ 3261-62-9 ]
  • [ 83793-44-6 ]
  • [ 179901-29-2 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 11
  • [ 77265-67-9 ]
  • [ 83793-44-6 ]
  • 4-[2-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-ethyl]-benzoic acid methyl ester [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 12
  • [ 41365-75-7 ]
  • [ 83793-44-6 ]
  • [ 615537-50-3 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3345 - 3350
  • 13
  • [ 83793-44-6 ]
  • 4-phenyl-<i>N</i>1-(4-piperidin-1-yl-phenyl)-butane-1,2-diamine [ No CAS ]
  • ((S)-3-Phenyl-1-{(S)-3-phenyl-1-[(4-piperidin-1-yl-phenylamino)-methyl]-propylcarbamoyl}-propyl)-carbamic acid benzyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 87 - 90
  • 14
  • [ 83793-44-6 ]
  • [ 62-53-3 ]
  • ((S)-3-Phenyl-1-phenylcarbamoyl-propyl)-carbamic acid benzyl ester [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 7172 - 7178
  • 15
  • [ 83793-44-6 ]
  • [ 2491-20-5 ]
  • (S)-2-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-propionic acid methyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5883 - 5887
  • 16
  • [ 83793-44-6 ]
  • [ 14316-06-4 ]
  • (R)-2-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-propionic acid methyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 5883 - 5887
  • 17
  • [ 83793-44-6 ]
  • 2-amino-4,<i>N</i>-diphenyl-butyramide [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 7172 - 7178
  • 18
  • [ 83793-44-6 ]
  • <i>N</i>2-benzyl-4,<i>N</i>1-diphenyl-butane-1,2-diamine [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 7172 - 7178
[2]Journal of Organic Chemistry,2005,vol. 70,p. 7172 - 7178
  • 19
  • [ 83793-44-6 ]
  • <i>N</i>-(3-phenyl-1-phenylaminomethyl-propyl)-benzamide [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 7172 - 7178
  • 20
  • [ 83793-44-6 ]
  • 2-benzylamino-4,<i>N</i>-diphenyl-butyramide [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 7172 - 7178
  • 21
  • [ 83793-44-6 ]
  • [ 865313-68-4 ]
Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 7172 - 7178
  • 22
  • [ 83793-44-6 ]
  • [ 615537-52-5 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3345 - 3350
  • 23
  • [ 83793-44-6 ]
  • (2S,3R)-2-[3-((S)-2-Amino-4-phenyl-butyrylamino)-propylamino]-3-{(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid tert-butyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3345 - 3350
  • 24
  • [ 83793-44-6 ]
  • [ 615537-54-7 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3345 - 3350
  • 25
  • [ 83793-44-6 ]
  • [ 1026863-19-3 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 26
  • [ 83793-44-6 ]
  • [ 1027543-59-4 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 27
  • [ 83793-44-6 ]
  • [ 1025878-38-9 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 28
  • [ 83793-44-6 ]
  • 2,N-Dihydroxy-N'-[(S)-3-phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-malonamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 29
  • [ 83793-44-6 ]
  • N-Hydroxy-2-isobutyl-N'-[(S)-3-phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-malonamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 30
  • [ 83793-44-6 ]
  • N-Hydroxy-N'-{(S)-1-[2-(4-hydroxy-phenyl)-ethylcarbamoyl]-3-phenyl-propyl}-2-isobutyl-malonamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 31
  • [ 83793-44-6 ]
  • 4-{2-[(S)-2-(2-Hydroxycarbamoyl-4-methyl-pentanoylamino)-4-phenyl-butyrylamino]-ethyl}-benzoic acid [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 32
  • [ 83793-44-6 ]
  • 2-Benzyl-N-hydroxy-N'-[(S)-3-phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-malonamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 33
  • [ 83793-44-6 ]
  • [ 202652-97-9 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 34
  • [ 83793-44-6 ]
  • N-Hydroxy-2-phenethyl-N'-[(S)-3-phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-malonamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 35
  • [ 83793-44-6 ]
  • N-Benzyloxy-2-isobutyl-N'-[(S)-3-phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-malonamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 36
  • [ 83793-44-6 ]
  • [ 1027979-35-6 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 37
  • [ 83793-44-6 ]
  • [ 1026045-48-6 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 38
  • [ 83793-44-6 ]
  • N-Benzyloxy-2-phenethyl-N'-[(S)-3-phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-malonamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 39
  • [ 83793-44-6 ]
  • [ 1026475-72-8 ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 40
  • [ 83793-44-6 ]
  • 2,N-Bis-benzyloxy-N'-[(S)-3-phenyl-1-(2-p-tolyl-ethylcarbamoyl)-propyl]-malonamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 339 - 345
  • 41
  • [ 83793-44-6 ]
  • (R)-2-{2-[(S)-1-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyryl)-pyrrolidin-2-yl]-2-oxo-acetylamino}-4-methyl-pentanoic acid tert-butyl ester [ No CAS ]
Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 900 - 908
  • 42
  • [ 83793-44-6 ]
  • (S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid [ No CAS ]
Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 890 - 899
  • 43
  • [ 83793-44-6 ]
  • [ 182742-38-7 ]
Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 890 - 899
  • 44
  • [ 501-53-1 ]
  • (+-)-2.3-diamino-propionic acid [ No CAS ]
  • [ 83793-44-6 ]
Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 890 - 899
  • 45
  • [ 90891-21-7 ]
  • [ 83793-44-6 ]
Reference： [1]Journal of Antibiotics,1996,vol. 49,p. 890 - 899
  • 46
  • [ 83793-44-6 ]
  • [ 1027065-31-1 ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 47
  • [ 83793-44-6 ]
  • [ 1026926-41-9 ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 48
  • [ 83793-44-6 ]
  • ((S)-3-Diazo-2-oxo-1-phenethyl-propyl)-carbamic acid benzyl ester [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 49
  • [ 83793-44-6 ]
  • [ 165727-48-0 ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 50
  • [ 83793-44-6 ]
  • [ 162538-21-8 ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 51
  • [ 83793-44-6 ]
  • [ 165727-49-1 ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 52
  • [ 83793-44-6 ]
  • [ 165727-47-9 ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 53
  • [ 83793-44-6 ]
  • ((S)-1-(R)-Oxiranyl-3-phenyl-propyl)-carbamic acid benzyl ester [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 54
  • [ 83793-44-6 ]
  • [ 162541-33-5 ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1758 - 1768
  • 55
  • [ 83793-44-6 ]
  • ((S)-2-Oxo-1-phenethyl-propyl)-carbamic acid benzyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 3745 - 3746
  • 56
  • [ 83793-44-6 ]
  • [ 146765-87-9 ]
Reference： [1]Journal of Pharmaceutical Sciences,1993,vol. 82,p. 1 - 10
  • 57
  • [ 83793-44-6 ]
  • [ 146765-98-2 ]
Reference： [1]Journal of Pharmaceutical Sciences,1993,vol. 82,p. 1 - 10
  • 58
  • [ 83793-44-6 ]
  • C20H29Cl2N5O4 [ No CAS ]
Reference： [1]Journal of Pharmaceutical Sciences,1993,vol. 82,p. 1 - 10
  • 59
  • [ 83793-44-6 ]
  • [ 146765-92-6 ]
Reference： [1]Journal of Pharmaceutical Sciences,1993,vol. 82,p. 1 - 10
  • 60
  • [ 83793-44-6 ]
  • (S)-2-Amino-N-[(S)-1-(2-chloro-ethylcarbamoyl)-2-methyl-propyl]-4-phenyl-butyramide; hydrobromide [ No CAS ]
Reference： [1]Journal of Pharmaceutical Sciences,1993,vol. 82,p. 1 - 10
  • 61
  • [ 83793-44-6 ]
  • [ 128625-52-5 ]
  • [ 6638-79-5 ]
  • benzyl 1S-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; Benzyl 1S-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate A solution of 2-benzyloxycarbonylamino-4-phenylbutyric acid (5.05 g, 16.1 mmol) in dichloromethane (70 mL) was cooled to 0 C. and treated with diisopropylethylamine (2.82 mL, 16.2 mmol) added dropwise and then PyBOP (8.53 g, 16.4 mmol) added in one portion. The mixture was stirred for 5 minutes and then treated with N,O-dimethylhydroxylamine hydrochloride (1.73 g, 17.71 mmol) added in one portion. The mixture was neutralized with diisopropylethylamine (4.6 mL, 26.44 mmol) added dropwise, stirred for 2 hours at room temperature and then diluted with dichloromethane (70 mL). The dilution was washed sequentially with 1N aqueous hydrochloric acid (3*40 mL), saturated sodium bicarbonate (3*40 mL) and brine (40 mL) and then concentrated. The product was purified from the residue by column chromatography eluding with 2:3 ethyl acetate/hexane to provide benzyl 1S-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate (5.48 g, 15.4 mmol) as an oil. MS(PCI) m/z=357 (M+1). Proceeding as in Reference 1 provided tert-butyl 1S-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate; 1H NMR (CDCl3): delta 1.35 (s, 9H), delta 1.64-1.72 (m, 2H), delta 2.40-2.54 (m, 1H), delta 2.60-2.77 (m, 1H), delta 3.00 (s, 3H) 3.52 (s, 3H), delta 4.23 (m, 1H), delta 7.10-7.37 (m, 5H).
With N-ethyl-N,N-diisopropylamine; In dichloromethane; Benzyl 1S-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate A solution of 2-benzyloxycarbonylamino-4-phenylbutyric acid (5.05 g, 16.1 mmol) in methylene chloride (70 mL) was cooled to 0 C. and treated with diisopropylethylamine (2.82 mL, 16.2 mmol) added dropwise and then PyBOP (8.53 g, 16.4 mmol) added in one portion. The mixture was stirred for 5 minutes and then treated with N,O-dimethylhydroxylamine hydrochloride (1.73 g, 17.71 mmol) was added in one portion. The mixture was neutralized with diisopropylethylamine (4.6 mL, 26.44 mmol) added dropwise, stirred for 2 hours at room temperature and then diluted with methylene chloride (70 mL). The dilution was washed with 1N aqueous hydrochloric acid (3*40 mL), saturated sodium bicarbonate (3*40 mL) and brine (40 mL) and then concentrated. The product was purified from the residue by column chromatography eluding with 2:3 ethyl acetatelhexane to provide benzyl 1S-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate (5.48 g, 15.4 mmol) as an oil. MS(PCI) m/z=357 (M+1). Proceeding as in Reference 13 provided tert-butyl 1S-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamate; 1H NMR (CDCl3): delta 1.35 (s, 9H), delta 1.64-1.72 (m, 2H), delta 2.40-2.54 (m, 1H), delta 2.60-2.77 (m, 1H), delta 3.00 (s, 3H) 3.52 (s, 3H), delta 4.23 (m, 1H), delta 7.10-7.37 (m, 5H).
Reference： [1]Patent: US6576630,2003,B1
[2]Patent: US6576630,2003,B1
  • 62
  • [ 83793-44-6 ]
  • [ 101651-14-3 ]
  • [ 205493-77-2 ]
YieldReaction ConditionsOperation in experiment
45% EXAMPLE 4 (3S,4S)-3-(N-benzyloxycarbonyl-L-homophenylalanyl)-amino-4-acetoxy-azetidin-2-one (4) By a similar method as described in example 1, the title compound was obtained by reacting N-benzyloxycarbonyl-L-homophenylalanine with (3S,4S)-3-amino-4-acetoxy-azetidin-2-one. Yield: 45%. m.p.: 180-181 C. FAB-MS: 440 (MH+), calcd for C23 H25 N3 O6 439 1 H NMR (DMSO-d6), delta (ppm): 1.75-1.95 (2H, m), 2.08 (3H, s), 2.60 (2H, m), 4.04 (1H, m), 4.65 (1H, d, J=8 Hz), 5.06 (2H, m), 5.76 (1H, s), 7.15-7.40 (10H, m), 7.65 (1H, d, J=8 Hz), 8.70 (1H, d, J=8 Hz), 9.18 (1H, s). IR (KBr, cm-1): 3310, 1802, 1748, 1687, 1660, 1555, 1532, 1367, 1242.
45% Example 4 (3S,4S)-3-(N-benzyloxycarbonyl-L-homophenylalanyl)-amino-4-acetoxy-azetidin-2-one (4) By a similar method as described in example 1, the title compound was obtained by reacting N-benzyloxycarbonyl-L-homophenylalanine with (3S,4S)-3-amino-4-acetoxy-azetidin-2-one. Yield: 45 %. m.p.: 180-181 C FAB-MS: 440 (MH+), calcd for C23H25N3O6 439 1H NMR (DMSO-d6), delta (ppm): 1.75-1.95 (2H, m), 2.08 (3H, s), 2.60 (2H, m), 4.04 (1H, m), 4.65 (1H, d, J=8 Hz), 5.06 (2H, m), 5.76 (1H, s), 7.15-7.40 (10H, m), 7.65 (1H, d, J=8 Hz), 8.70 (1H, d, J=8 Hz), 9.18 (1H, s). IR (KBr, cm-1): 3310, 1802, 1748, 1687, 1660, 1555, 1532,1367, 1242.
Reference： [1]Patent: US5959123,1999,A
[2]Patent: EP950046,2002,B1
  • 63
  • [ 83793-44-6 ]
  • (S)-[1-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]carbonyl]-3-phenylpropyl]carbamic acid phenylmethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 2 Preparation of (S)-[1-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)amino]carbonyl]-3-phenylpropyl]carbamic acid phenylmethyl ester STR8 Following the general procedure outlined in method A, and making non critical variations but starting with Cbz-L-homophenylalanine, the title compound is obtained as a white solid. 1 H NMR (DMSO-d6) delta 6 1.89, 2.65, 4.23, 5.06, 7.15-7.39, 7.93, 12.63, 14.10; 13 C NMR (DMSO-d6) ppm 31.5, 32.7, 54.3, 65.6, 125.8, 127.7, 127.8, 128.2, 128.3, 136.7, 140.7, 151.9, 156.0, 172.1, 183.6; IR (mull) 3332, 2362, 2187, 1950, 1691, 1575, 1525, 1304, 1276, 1268, 1250, 1070, 1048, 750, 700 cm-1; MS (EI) m/z 428 (M+), 428, 224, 223, 134, 133, 117, 92, 91, 76, 65.
Example 2 Preparation of (S)-[1-[[(4,5-dihydro-5-thioxo-1,3,4-thiadiazol-2-yl)-amino]carbonyl]-3-phenylpropyl]carbamic acid phenylmethyl ester Following the general procedure outlined in method A, and making non critical variations but starting with Cbz-L-homophenylalanine, the title compound is obtained as a white solid. 1H NMR (DMSO-d6) delta 1.89, 2.65, 4.23, 5.06, 7.15-7.39, 7.93, 12.63, 14.10; 13C NMR (DMSO-d6) ppm 31.5, 32.7, 54.3, 65.6, 125.8, 127.7, 127.8, 128.2, 128.3, 136.7, 140.7, 151.9, 156.0, 172.1, 183.6; IR (mull) 3332, 2362, 2187, 1950, 1691, 1575, 1525, 1304, 1276, 1268, 1250, 1070, 1048, 750, 700 cm-1; MS (EI) m/z 428 (M+), 428, 224, 223, 134, 133, 117, 92, 91, 76, 65.
Reference： [1]Patent: US5830869,1998,A
[2]Patent: EP1021424,2003,B1
  • 64
  • [ 83793-44-6 ]
  • [ 144-55-8 ]
  • [ 282110-53-6 ]
YieldReaction ConditionsOperation in experiment
100% With p-toluenesulfonic acid monohydrate; paraformaldehyde; In toluene; 1.1 Synthesis of 4-phenethyl-3-(carbobenzyloxy)oxazolidin-5-one Combine N-(carbobenzyloxy)-(L)-homophenylalanine (5.00 g. 16.0 mmol) and paraformaldehyde (1.44 g, 48.0 mmol) in toluene (75 mL). Add p-toluenesulfonic acid monohydrate (300 mg). Heat at reflux using a Dean-Stark trap to remove water. After 45 minutes, cool the reaction mixture. Concentrate the cooled reaction mixture in vacuo to give a residue. Partition the residue between methyl t-butyl ether (150mL) and a mixture of saturated aqueous sodium bicarbonate solution and brine (1/1=50 mL). Separate the organic layer, dry over Na2SO4, filter, and concentrated in vacuo to give the title compound (5.18 g, 100%).
100% With p-toluenesulfonic acid monohydrate; paraformaldehyde; In toluene; 1.1 Synthesis of 4-phenethyl-3-(carbobenzyloxy)oxazolidin-5-one Combine N-(carbobenzyloxy)-(L)-homophenylalanine (5.00 g. 16.0 mmol) and paraformaldehyde (1.44 g, 48.0 mmol) in toluene (75 mL). Add p-toluenesulfonic acid monohydrate (300 mg). Heat at reflux using a Dean-Stark trap to remove water. After 45 minutes, cool the reaction mixture. Concentrate the cooled reaction mixture in vacuo to give a residue. Partition the residue between methyl t-butyl ether (150 mL) and a mixture of saturated aqueous sodium bicarbonate solution and brine (1/1=50 mL). Separate the organic layer, dry over Na2SO4, filter, and concentrated in vacuo to give the title compound (5.18 g, 100%).
Reference： [1]Patent: EP1150976,2003,B1
[2]Patent: US6262080,2001,B1
  • 65
  • [ 83793-44-6 ]
  • [ 2812-46-6 ]
  • C27H34N2O5 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7830 - 7839
  • 66
  • [ 1073842-94-0 ]
  • [ 83793-44-6 ]
  • [ 1075237-95-4 ]
Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 8458 - 8468
  • 67
  • [ 945606-90-6 ]
  • [ 83793-44-6 ]
  • [ 1094442-20-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5895 - 5899
  • 68
  • [ 83793-44-6 ]
  • [ 1366127-32-3 ]
Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3163 - 3169
  • 69
  • [ 83793-44-6 ]
  • [ 207305-48-4 ]
Reference： [1]Organic Process Research and Development,1998,vol. 2,p. 186 - 193
  • 70
  • [ 943-73-7 ]
  • [ 42940-68-1 ]
  • [ 83793-44-6 ]
Reference： [1]Organic Process Research and Development,1998,vol. 2,p. 186 - 193
  • 71
  • [ 1569294-31-0 ]
  • [ 83793-44-6 ]
  • [ 1569294-41-2 ]
Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1274 - 1279
  • 72
  • C5H7BrN2O [ No CAS ]
  • [ 83793-44-6 ]
  • benzyl (2S)-1-(3-bromo-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazol-5-yl)-1-oxo-4-phenylbutan-2-ylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; General procedure: To a solution of the N-protected carboxylic acid (1 equiv) inDMF/CH2Cl2 (1:1), HOBt (1.2 equiv), EDCI (1.2 equiv), amine42,11a (1 equiv) and DIPEA (1.5 equiv) were added at 0 C. Thereaction mixture was stirred for 15 h, diluted with EtOAc,washed with a saturated solution of NaHCO3, dried over Na2SO4and concentrated in vacuo. The crude product was then purifiedby flash column chromatography by using as eluent a mixture oflight petroleum/EtOAc (6:4) to give the diastereomeric mixtures 1-12a,b
Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7053 - 7060
  • 73
  • [ 106860-17-7 ]
  • [ 83793-44-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7053 - 7060
  • 74
  • [ 501-53-1 ]
  • [ 83793-44-6 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7053 - 7060
  • 75
  • [ 142037-77-2 ]
  • [ 83793-44-6 ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxide; In methanol; water; at 0 - 20℃; for 8h; General procedure: To a solution of the carbamates obtained in the previous step(1 equiv) in a mixture methanol/water (1:1), LiOH (2 equiv) wasadded at 0 C. The reaction mixture was then stirred at rt, until disappearanceof the starting material (TLC monitoring). The solventwas then concentrated in vacuo and the reaction mixture was treatedwith 10% citric acid, extracted with EtOAc, dried over Na2SO4and concentrated to afford the pure carboxylic acids
Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 7053 - 7060
  • 76
  • [ 83793-44-6 ]
  • methyl (2S)-2-[(N-{(2S)-2-amino-4-[(tert-butoxycarbonyl)amino]butanoyl}-L-threonyl)amino]-4-[(tert-butoxycarbonyl)amino]butanoate [ No CAS ]
  • (2S)-2-[(N-{(2S)-2-[(2S)-2-[(benzyloxy)carbonyl]amino}-4-phenylbutanoyl]amino}-4-[(tert-butoxycarbonyl)amino]butanoyl}-L-threonyl)amino]-4-[(tert-butoxycarbonyl)amino]butanoic acid [ No CAS ]
Reference： [1]Patent: WO2017/218922,2017,A2 .Location in patent: Page/Page column 181
  • 77
  • [ 83793-44-6 ]
  • C17H37NO3Si [ No CAS ]
  • C35H54N2O6Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.85 g With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0℃; for 2h; [0488] To a mixture of 3-33-3 (0.473 g, 1.51 mmol) in dichloromethane (6 mL) was added diisopropylethylamine (0.66 mL, 3.8 mmol) and T3P (1.35 mL, 2.26 mmol, 50% solution in EtOAc) at 0C. To this was added <strong>[83793-44-6](S)-2-(((benzyloxy)carbonyl)amino)-4-phenylbutanoic acid</strong> (0.500 g, 1.51 mmol) and the reaction mixture was stirred at 0C for 2 hours. The mixture was diluted with 30 mL of dichloromethane, washed with a saturated aqueous sodium carbonate solution then dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography and the eluent removed under reduced pressure to afford 3-33-4 (0.850 g, 1.36 mmol) as a colorless oil.
Reference： [1]Patent: WO2019/75259,2019,A1 .Location in patent: Paragraph 0488
  • 78
  • [ 83793-44-6 ]
  • [ 380848-17-9 ]
  • benzyl ((S)-1-oxo-4-phenyl-1-((S)-5-phenylpent-1-en-3-ylamino)butan-2-yl)carbamate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 10617 - 10629
  • 79
  • [ 83793-44-6 ]
  • [ 380848-17-9 ]
  • benzyl ((S)-1-oxo-1-((S,E)-6-oxo-1-phenylhept-4-en-3-ylamino)-4-phenylbutan-2-yl)carbamate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 10617 - 10629

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