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Chemical Structure| 51019-43-3 Chemical Structure| 51019-43-3
Chemical Structure| 51019-43-3

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Product Details of (R)-2-Acetoxy-2-phenylacetic acid

CAS No. :51019-43-3
Formula : C10H10O4
M.W : 194.18
SMILES Code : O=C(O)[C@H](OC(C)=O)C1=CC=CC=C1
MDL No. :MFCD00004249
InChI Key :OBCUSTCTKLTMBX-SECBINFHSA-N
Pubchem ID :2733814

Safety of (R)-2-Acetoxy-2-phenylacetic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of (R)-2-Acetoxy-2-phenylacetic acid

* 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 [ 51019-43-3 ]

[ 51019-43-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 51019-43-3 ]
  • [ 15996-84-6 ]
  • [ 581812-92-2 ]
  • [ 581812-91-1 ]
YieldReaction ConditionsOperation in experiment
33%; 36% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 16h; DCC (2.35 g, 12.1 mmol) and DMAP (50 mg) were added to a stirred solution of (RS)-117 (2.29 g, 12.1 mmol) and (R)-O-acetylmandelic acid (2.35 g, 12.1 mmol, >99:1 er) in CH2Cl2 (60 mL) at 0 C and the resultant mixture was stirred at rt for 16 h. The reaction mixture was filtered and the filtrate was washed sequentially with 1.0 M aq HCl (40 mL), satd aq NaHCO3 (40 mL) and brine (40 mL), then dried and concentrated in vacuo. Purification via flash column chromatography (eluent 30-40 C petrol/EtOAc, 2:1, 1% Et3N) gave 119 as a white solid (1.58 g, 36%, >99:1 dr); mp 132.5-133.5 C; νmax (ATR) 3292 (N-H), 1742, 1662 (C=O), 1327 (C-F); [α]D20 -153.0 (c 1.0 in MeOH); δH (500 MHz, CDCl3) 1.40 (3H, d, J 7.0, C(α)Me), 2.13 (3H, s, COMe), 4.87 (1H, br s, NH), 5.00 (1H, q, J 7.0, C(α)H), 5.94 (1H, s, C(2)H), 7.33-7.39 (3H, m, C(2')H, C(6')H, Ph), 7.48-7.53 (4H, m, Ph), 7.58 (2H, d, J 8.2, C(3')H, C(5')H); δC (125 MHz, CDCl3) 20.8 (COMe), 22.1 (C(α)Me), 50.0 (C(α)), 77.2 (C(2)), 125.9 (q, J 269.9, CF3), 126.4 (q, J 3.8, C(3'), C(5')), 127.9 (C(2'), C(6')), 128.7 (o-Ph), 129.8 (m-Ph), 130.2 (p-Ph), 130.3 (q, J 31.5, C(4')), 136.8 (i-Ph), 149.5 (C(1')), 171.0 (C(1)), 172.1 (COMe); δF (377 MHz, CDCl3) -63.9 (CF3); m/z (ESI+) 388 ([M+Na]+, 100%); HRMS (ESI+) ([M+Na]+) requires 388.1131; found 388.1122. Further elution gave 118 as a white solid (1.46 g, 33%, >99:1 dr); mp 118-120 C; νmax (ATR) 3291 (N-H), 1744, 1663 (C=O), 1327 (C-F); [α]D20 -17.0 (c 1.0 in MeOH); δH (500 MHz, CDCl3) 1.47 (3H, d, J 7.0, C(α)Me), 2.15 (3H, s, COMe), 4.87 (1H, br s, NH), 5.06 (1H, q, J 7.0, C(α)H), 5.94 (1H, s, C(2)H), 7.24 (2H, d, J 8.4, C(2')H, C(6')H), 7.34-7.38 (3H, m, Ph), 7.44-7.49 (4H, m, C(3')H, C(5')H, Ph); δC (125 MHz, CDCl3) 20.8 (COMe), 22.0 (C(α)Me), 50.0 (C(α)), 77.1 (C(2)), 125.7 (q, J 270.8, CF3), 126.4 (q, J 3.8, C(3'), C(5')), 127.6 (C(2'), C(6')), 128.8 (o-Ph), 129.8 (m-Ph), 130.2 (p-Ph), 130.3 (q, J 32.4, C(4')), 136.7 (i-Ph), 149.5 (C(1')), 170.9 (C(1)), 172.1 (COMe); δF (377 MHz, CDCl3) -63.7 (CF3); m/z (ESI+) 388 ([M+Na]+, 100%); HRMS (ESI+) ([M+Na]+) requires 388.1131; found 388.1120. A 57:43 mixture of 118 and 119, respectively, was also recovered as a white solid (812 mg, 18%).
 

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