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

HRID 222449ノート

反応式

HRID 222449 の反応式
[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]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 679Dimethyl Sulfoxide2 回HCID 8471TriethylamineHCID 57351319Ethyl (4R)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentanoate

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-052e1632a2c44812bd295e9f2c245524
出典データセット
uspto-grants-2012_06
特許番号
US08207223B2

反応ノート

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