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

HRID 421186노트

반응식

HRID 421186 반응식
[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]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 4247255tert-butyl N-(2-oxoethyl)carbamate2회HCID 5049666Sodium triacetoxyborohydride2회HCID 592157783-Thiomorpholinecarboxylic acid, methyl ester, 1,1-dioxide

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f9357c5dc51a46098b1bd752b622cc80
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097618B2

반응 노트

불러오는 중…