Hydrochloric Acid → ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate

HRID 222449노트

반응식

HRID 222449 반응식
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C@@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][OH:9])[CH3:2].C(N(CC)CC)C.CS(C)=O.Cl>C(OCC)(=O)C.O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C@@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:8]=[O:9])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 679Dimethyl Sulfoxide2회HCID 8471TriethylamineHCID 57351319Ethyl (4R)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentanoate

생성물 1

HCID 57894011ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate수율 98.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

Under atmosphere of argon, to a solution of (4R)-5-hydroxy-4-t-butoxycarbonylaminopentanoic acid ethyl ester (15.0 g), triethylamine (32.0 mL) and dimethylsulfoxide (39 mL) in ethyl acetate (120 mL), a solution of sulfur trioxide pyridine complex (18.3 g) in mixed solvent ethyl acetate (30 mL) and dimethylsulfoxide (75 mL) was added at 0° C., and the mixture was stirred for 1 hour. The reaction mixture was added by water (5 mL) at 0° C. and was added by 1N hydrochloric acid (240 mL). Separated aqueous layer was extracted by ethyl acetate. The combined organic layer was washed with water and brine successively, dried over an anhydrous sodium sulfate, concentrated under reduced pressure to give the title compound (14.7 g) having the following physical data.

후처리

  1. extractionSeparated aqueous layer was extracted by ethyl acetate
  2. washThe combined organic layer was washed with water and brine successively
  3. dry with materialdried over an anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-052e1632a2c44812bd295e9f2c245524
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207223B2

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