Acetic Acid → Methyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-3-thiomorpholinecarboxylate 1,1-dioxide

HRID 421186ノート

反応式

HRID 421186 の反応式
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH:2]1[C:9]([O:11][CH3:12])=[O:10].[C:13]([NH:20][CH2:21][CH:22]=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:17][C:16]([O:15][C:13]([NH:20][CH2:21][CH2:22][N:1]1[CH2:6][CH2:5][S:4](=[O:7])(=[O:8])[CH2:3][CH:2]1[C:9]([O:11][CH3:12])=[O:10])=[O:14])([CH3:19])[CH3:18]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 4247255tert-butyl N-(2-oxoethyl)carbamate2 回HCID 5049666Sodium triacetoxyborohydride2 回HCID 592157783-Thiomorpholinecarboxylic acid, methyl ester, 1,1-dioxide

生成物 1

HCID 59215870Methyl 4-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-3-thiomorpholinecarboxylate 1,1-dioxide収率 15.7%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a stirred solution of methyl 3-thiomorpholinecarboxylate 1,1-dioxide (D16; 1.08 g, 5.6 mmol) in 14 ml of anhydrous 1,2-dichloroethane was added N-boc-2-aminoacetaldehyde (1.1 g, 6.7 mmol) and acetic acid (0.316 ml, 5.6 mmol). After 30 min. sodium triacetoxyborohydride (1.78 g, 8.4 mmol) was added and the solution stirred at room temperature. Additional aliquots of N-boc-2-aminoacetaldehyde and sodium triacetoxyborohydride (1.0 g, 4.7 mmol) were added and the reaction continued overnight. The solvent was removed under reduced pressure and the residue was purified by SCX column, followed by chromatography (silica, cyclohexane:ethyl acetate 70:30 to 1:1) and again SCX, to give 295 mg of the target compound.

後処理

  1. customthe reaction continued overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by SCX column

出典と根拠

ORDレコード
ord-f9357c5dc51a46098b1bd752b622cc80
出典データセット
uspto-grants-2012_01
特許番号
US08097618B2

反応ノート

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