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

HRID 4422노트

반응식

HRID 4422 반응식
[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]

참가 물질

7

반응물 5

HCID 180Acetone2회HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 540061222-Benzyloxycarbonyloxyimino-2-phenylacetonitrileHCID 131713573Boc-L-Ala-D-Glu(OH)OMe

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-cb80480d56a947c299041233295b2f80
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725582

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