p-Toluenesulfonic acid → HCID 86653082、化合物

HRID 1254316ノート

反応式

HRID 1254316 の反応式
C(OC([NH:8][C@H:9]([CH2:12][N:13]([CH3:23])[C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[CH2:10][OH:11])=O)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC.C(O)C>[NH2:8][C@@H:9]([CH2:10][OH:11])[CH2:12][N:13]([CH3:23])[C:14](=[O:15])[O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]

参加物

5

反応物 2

HCID 6101p-Toluenesulfonic acid2 回HCID 86653083HCID 86653083、化合物

生成物 1

HCID 86653082HCID 86653082、化合物収率 90%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
62.5 °C

実験手順

To a solution of (2R)-2-(t-butoxycarbonylamino)-3-(N-methyl-N-(2-(trimethylsilyl)-ethoxycarbonyl)amino)propan-1-ol (0.55 g, 1.58 mmol) in ether (5 mL) was added a solution of p-toluenesulfonic acid (0.31 g, 1.60 mmol) in ethanol (2 mL). Transfer of the p-toluenesulfonic acid was completed with the aid of ether (1 mL). The solution was placed on a rotary evaporator and the ether removed under vacuum at rt. Then, with continuing evacuation, the bath temperature was raised to 60-65° C. for 30 min, during which gas evolution was evident. The solid residue was dissolved in 1 N aq NaOH solution (5 mL) and extracted with CH2Cl2 (4×5 mL). The combined organic layers were washed with brine and dried over Na2SO4. Solvent was removed in vacuo to give (2-(trimethylsilyl)ethyl) (R)-2-amino-3-hydroxypropyl-methylcarbamate (0.35 g, 90%) as a free amine, which was without purification. MS m/z 249 (M+H+).

後処理

  1. customThe solution was placed on a rotary evaporator
  2. customthe ether removed under vacuum at rt
  3. dissolutionThe solid residue was dissolved in 1 N aq NaOH solution (5 mL)
  4. extractionextracted with CH2Cl2 (4×5 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customSolvent was removed in vacuo

出典と根拠

ORDレコード
ord-04e6fc55e76f4177bde7439f89223bbc
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

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