Hydrochloric Acid → 2-Tert-butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester

HRID 987936

反応式

HRID 987936 の反応式
[CH3:1][O:2][C:3](=[O:15])[C@@H:4]([CH2:13][OH:14])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl.C(N(CC)CC)C.[S:24](Cl)([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25].C(N(CC)CC)C.Cl>ClCCl.CN(C)C1C=CN=CC=1.O>[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])[CH2:13][O:14][S:24]([C:27]1[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=1)(=[O:26])=[O:25]

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 377723N-Boc-D-serine methyl ester

生成物 1

HCID 28181622-Tert-butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester収率 67.1%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
6 °C

実験手順

A solution of Boc-D-serine methyl ester (9.59 g, 43.8 mmol) in dichloromethane (100 ml) was stirred at −10° C. during the addition of 4-(dimethylamino)pyridine (270 mg, 2.19 mmol), triethylamine hydrochloride (4.19 g, 43.8 mmol) and tosyl chloride (8.35 g, 43.8 mmol). Triethylamine (6.10 ml, 43.8 mmol) was added dropwise at −10° C. over 35 minutes and the resultant slurry was allowed to stand at 6° C. overnight. The reaction mixture was poured into a mixture of ice (35 g), water (35 ml) and 2N hydrochloric acid (20 ml). The aqueous phase was extracted with dichloromethane (35 ml) and the combined organic solutions washed with brine (2*25 ml), dried (anhydrous magnesium sulfate) and concentrated in vacuo to a pale yellow oil. The oil was dissolved in diethyl ether (100 ml) and cooled to 6° C. Once crystallisation started, petrol ether (75 ml) was added in five portions over two hours, and crystallisation was allowed to proceed at 6° C. overnight to give 2-tert-butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester (10.98 g, 67%).

後処理

  1. extractionThe aqueous phase was extracted with dichloromethane (35 ml)
  2. washthe combined organic solutions washed with brine (2*25 ml)
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. concentrationconcentrated in vacuo to a pale yellow oil
  5. dissolutionThe oil was dissolved in diethyl ether (100 ml)
  6. customOnce crystallisation
  7. additionpetrol ether (75 ml) was added in five portions over two hours
  8. customcrystallisation
  9. waitto proceed at 6° C. overnight

出典と根拠

ORDレコード
ord-421fe8c6e1644077bac92f1a51c9a832
出典データセット
uspto-grants-2003_10
特許番号
US06632826B1

関連ノート

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