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Chemical Structure| 537697-19-1 Chemical Structure| 537697-19-1

Structure of 537697-19-1

Chemical Structure| 537697-19-1

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Product Details of [ 537697-19-1 ]

CAS No. :537697-19-1
Formula : C10H21NO4
M.W : 219.28
SMILES Code : O=C(OC(C)(C)C)N[C@@H]([C@H](OC)C)CO

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Application In Synthesis of [ 537697-19-1 ]

* 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 [ 537697-19-1 ]

[ 537697-19-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 48068-25-3 ]
  • [ 543-27-1 ]
  • [ 537697-19-1 ]
YieldReaction ConditionsOperation in experiment
Part A. ((lR,2R)-l-Hydroxymethyl-2-methoxy-propyl)-carbamic acid tert-butyl ester To a cold solution (-15C) of BocThr(Me)OH (5.14 g, 22 mmol) in dichloroethane (22 mL) were successively added N-methyl morpholine (2.44 mL, 22 mmol) and isobutyl chloroformate (2.99 mL, 22 mmol). After one min, the precipitate was filtered and washed with dichloroethane (5 x 4mL). The filtrate and washings were combined in a large three neck flask in an ice-salt bath. A solution of NaBH4 (1.26 g, 33 mmol) in H2O (11 mL) was added at once, proceeding a strong evolution of gas, followed by H20 (500 mL). The mixture was then extracted with EtOAc (5 x 150 mL). The combined EtOAc was dried ( a2S04) and concentrated to give the titled compound (5 g). MS (MH+ 220).
  • 2
  • [ 48068-25-3 ]
  • [ 537697-19-1 ]
YieldReaction ConditionsOperation in experiment
85% Step 1To a round bottom flask containing a stir bar and (25,3R)-2-((tert-butoxycarbonyl)amino)-3-methoxybutanoic acid (2.5 g, 10.7 mmol) in THF (80 mL) under nitrogen was cooled to -30 00in a dry ice/acetone bath. To this cold solution was added isobutyl chloroformate (1.7 mL, 12.9mmol) followed by the addition of N-methylmorpholine (1.4 mL, 12.9 mmol). Mixture wasstirred for 15 mm at -30 00 N-Methylmorpholine salt develops and was filtered from mixture. Mother liquor was cooled to -30 00 where upon sodium borohydride (0.61 g, 16.1 mmol) was added followed by the addition of water (10 mL) immediately afterwards. Reaction mixture allowed to stir for 15 mm at -20 00 then gradually allowed to warm to room temperature.Reaction mixture was stirred for 30 mm at room temperature. Reaction mixture was then diluted with water and extracted with EtOAc. Organic phases combined, washed with water, brine, dried (Na2504), filtered and concentrated to afford tert-butyl ((2R,3R)-1-hydroxy-3- methoxybutan-2-yl)carbamate (2.0 g, 9.1 mmol, 85 % yield) as a coloreless oil. 1H NMR (400 MHz, ODd3) oe 1.18 (d, J=6.26 Hz, 3 H) 1.45 (5, 9 H) 3.33 (5, 3 H) 3.55 - 3.84 (m, 4 H).LOMS m/z 220.2 (M + H), Rt 0.57 mm.
 

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