Acetone → stearoyl-L-Ala-D-Glu(OH)OBzl

HRID 4422ノート

反応式

HRID 4422 の反応式
[NH:1]([C:17]([O:19]C(C)(C)C)=O)[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3].C(N([CH2:29][CH3:30])CC)C.C(OC(ON=[C:43]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:44]#N)=O)C1C=CC=CC=1.C(O[CH2:56][CH3:57])(=O)C.[CH3:58][C:59]([CH3:61])=O>O>[NH:1]([C:17]([CH2:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:46][CH2:43][CH2:44][CH2:56][CH2:57][CH2:29][CH3:30])=[O:19])[C@H:2]([C:4]([NH:6][C@@H:7]([C:13]([O:15][CH2:16][C:59]1[CH:61]=[CH:4][CH:2]=[CH:3][CH:58]=1)=[O:14])[CH2:8][CH2:9][C:10](=[O:12])[OH:11])=[O:5])[CH3:3]

参加物

7

反応物 5

HCID 180Acetone2 回HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 540061222-Benzyloxycarbonyloxyimino-2-phenylacetonitrileHCID 131713573Boc-L-Ala-D-Glu(OH)OMe

生成物 1

HCID 131713574stearoyl-L-Ala-D-Glu(OH)OBzl収率 94.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

To a solution of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-mesoDAP-(L)-GlyOH (1) (1.2 g) in water (5 ml) was added triethylamine (0.96 g) and a solution of benzyloxycarbonyloxyimino-2-phenylacetonitrile (0.69 g) in acetone (5 ml) at 0° C. with stirring and the mixture was stirring over night at room temperature. After evapolation of acetone to the residue was added water (5 ml) and ethyl acetate (5 ml). The aqueous layer was separated, washed with ethyl acetate (5 ml), acidified with 1N-hydrochloric acid, and extracted with ethyl acetate (20 ml). The extract was washed with water (5 ml×2) and dried over magnesium sulfate. Evaporation of the solvent gave 1.42 g (94.7%) of D-Lac-L-Ala-γ-D-Glu(α-OH)-(L)-Z-(D)-mesoDAP-(L)-GlyOH (2). ##STR551##

後処理

  1. customThe aqueous layer was separated
  2. washwashed with ethyl acetate (5 ml)
  3. extractionextracted with ethyl acetate (20 ml)
  4. washThe extract was washed with water (5 ml×2)
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-cb80480d56a947c299041233295b2f80
出典データセット
uspto-grants-1988_02
特許番号
US04725582

反応ノート

読み込み中…