Sodium Bicarbonate → cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-hydroxymethyl-2-oxoazetidine

HRID 465260노트

반응식

HRID 465260 반응식
[NH2:1][C@H:2]1[C@@H:5]([CH2:6][OH:7])[NH:4][C:3]1=[O:8].C(=O)([O-])O.[Na+].Cl.[Cl:15][CH2:16][C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23](/[C:25](=[N:29]/[O:30][CH3:31])/[C:26](Cl)=[O:27])[N:24]=1)=[O:18]>O1CCCC1.O>[Cl:15][CH2:16][C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25](=[N:29][O:30][CH3:31])[C:26]([NH:1][C@H:2]2[C@@H:5]([CH2:6][OH:7])[NH:4][C:3]2=[O:8])=[O:27])[N:24]=1)=[O:18]

참가 물질

6

반응물 3

HCID 516892Sodium Bicarbonate2회HCID 12884125(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl chloride;hydrochlorideHCID 20632011cis-3-Amino-4-hydroxymethyl-2-oxoazetidine

생성물 1

HCID 86740477cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-hydroxymethyl-2-oxoazetidine

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

In a mixture of 2 ml of tetrahydrofuran and 2 ml of water is dissolved 75 mg of cis-3-amino-4-hydroxymethyl-2-oxoazetidine as obtained in Reference Example 53C and, under ice-cooling and stirring 168 mg of sodium hydrogen carbonate and then 332 mg of 2-(2-chloroacetamido-4-thiazolyl)-(Z)-2-methoxyiminoacetyl chloride hydrochloride are added. The mixture is stirred under ice-cooling for one hour and the reaction mixture is made neutral with aqueous sodium hydrogen carbonate and extracted with ethyl acetate-tetrahydrofuran (2:1). The extract is washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and, after addition of ethyl acetate-ether (1:2), the crystalline residue is recovered by filtration to give cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-hydroxymethyl-2-oxoazetidine (syn-isomer) as colorless crystals, m.p. 238°-241° C. (decomp.).

후처리

  1. customas obtained in Reference Example 53C and, under ice-
  2. temperaturecooling
  3. temperaturecooling for one hour
  4. extractionextracted with ethyl acetate-tetrahydrofuran (2:1)
  5. washThe extract is washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent is then distilled off under reduced pressure
  8. additionafter addition of ethyl acetate-ether (1:2)
  9. filtrationthe crystalline residue is recovered by filtration

출처 및 근거

ORD 기록
ord-886d74d9b85243d1840ea322110cfdf2
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04550105

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