Benzyl chloroformate → 2-{[(Benzyloxy)carbonyl]amino}-3-(thiophen-2-yl)propanoic acid

HRID 356714

反応式

HRID 356714 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[NH2:8].C([O-])([O-])=O.[K+].[K+].[C:18](Cl)([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].CCOC(C)=O.CC(O)=O.CC#N.O>O>[CH2:21]([O:20][C:18]([NH:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 914442-ThienylalanineHCID 131719237EtOAc AcOH CH3CN H2O

生成物 1

HCID 128068302-{[(Benzyloxy)carbonyl]amino}-3-(thiophen-2-yl)propanoic acid収率 98%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Into a 500 ml flask was placed 3.0 g of 3-(2-Thienyl)-D,L-alanine (optically active material in the L-form is available from Aldrich or SIGMA and could be used to obtain an optically active product) in 75 ml H2O/60 ml dioxane, and 5.6 g K2CO3 was added, followed by 2.85 ml of carbobenzyloxy chloride. The mixture was stirred rapidly for 1 hour. TLC (21/7/7/9, EtOAc/AcOH/CH3CN/H2O; showed that the starting material was gone. A new higher Rf product was seen. The dioxane was concentrated off and the aqueous layer was washed with Et2O (75 ml). The aqueous layer was mixed with CH2Cl2 (150 ml) and acidified to pH=2.0 with 5N HCl. The desired N-(Benzyloxycarbonyl)-3-(2-thienyl)-D,L-alanine was extracted with CH2Cl2. The organic layer was separated and dried with Na2SO4, filtered, and concentrated to give 5.05 g of desired N-(Benzyloxycarbonyl)-3-(2-thienyl)-D,L-alanine (98% yield).

後処理

  1. customInto a 500 ml flask was placed
  2. concentrationThe dioxane was concentrated off
  3. washthe aqueous layer was washed with Et2O (75 ml)
  4. additionThe aqueous layer was mixed with CH2Cl2 (150 ml)
  5. extractionThe desired N-(Benzyloxycarbonyl)-3-(2-thienyl)-D,L-alanine was extracted with CH2Cl2
  6. customThe organic layer was separated
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-c4f3c98e684348dd8340583a66282c99
出典データセット
uspto-grants-1998_11
特許番号
US05837710

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