Tetrahydrofuran → sodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1649769노트

반응식

HRID 1649769 반응식
[NH2:1][C@@H:2]1[C:14](=[O:15])[N:4]2[C:5]([C:11]([OH:13])=[O:12])=[C:6]([CH2:9][OH:10])[CH2:7][S:8][C@H:3]12.[OH-].[Na+:17].S1C2C=CC=CC=2N=C1S[O:28][C:29](=O)/[C:30](/[C:52]1[N:53]=[C:54]([NH:57][C:58]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[S:55][CH:56]=1)=[N:31]\[O:32][C:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O1CCCC1>O.C(#N)C.O1CCOCC1>[C:58]([NH:57][C:54]1[S:55][CH:56]=[C:52](/[C:30](=[N:31]/[O:32][C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)/[C:29]([NH:1][C@@H:2]2[C:14](=[O:15])[N:4]3[C:5]([C:11]([O-:13])=[O:12])=[C:6]([CH2:9][OH:10])[CH2:7][S:8][C@H:3]23)=[O:28])[N:53]=1)([C:71]1[CH:72]=[CH:73][CH:74]=[CH:75][CH:76]=1)([C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1.[Na+:17]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11031679(6R-trans)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidHCID 884755391,3-benzothiazol-2-ylsulfanyl (2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetate

생성물 1

HCID 23676286sodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매

실험 절차

In 20 ml of water is suspended 260 mg of 7β-amino-3-hydroxymethyl-3-cephem-4-carboxylic acid, and with ice-cooling and stirring, the suspension is adjusted to pH 7.0 with 1N-aqueous sodium hydroxide solution. After dissolution, 930 mg of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(trityloxyimino)acetic acid benzothiazol-2-ylthio ester, 20 ml of tetrahydrofuran, 20 ml of dioxane and 10 ml of acetonitrile are added and the mixture is stirred at room temperature for 38 hours. The reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is dissolved in 30 ml of tetrahydrofuran and the solution is subjected to silica gel (100 g) column chromatography. After the column is washed with acetonitrile (500 ml) and acetonitrile-water (19:1, 200 ml; 9:1, 200 ml), elution is carried out with 300 ml of acetonitrile-water (17:3). The eluate is concentrated under reduced pressure and the concentrate is freeze-dried to give 420 mg of sodium 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-(trityloxyimino)acetamido]-3-hydroxymethyl-3-cephem-4-carboxylate as light yellow powders.

후처리

  1. temperaturewith ice-cooling
  2. additionare added
  3. stirringthe mixture is stirred at room temperature for 38 hours
  4. filtrationThe reaction mixture is filtered
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. dissolutionThe residue is dissolved in 30 ml of tetrahydrofuran
  7. washAfter the column is washed with acetonitrile (500 ml) and acetonitrile-water (19:1, 200 ml; 9:1, 200 ml), elution
  8. concentrationThe eluate is concentrated under reduced pressure
  9. customthe concentrate is freeze-dried

출처 및 근거

ORD 기록
ord-e3584286636d428ab14d7af07e0a1912
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04921851

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