Trifluoroacetic acid → (2S-trans)[1-[[2-(3-Amino-2-oxo-1-imidazolidinyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

HRID 4120

반응식

HRID 4120 반응식
CC(C)(OC([NH:7][N:8]1[CH2:12][CH2:11][N:10]([C:13](=[O:36])[CH2:14][O:15][P:16]([OH:35])([N:18]2[C:21](=[O:22])[C@@H:20]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:19]2[CH3:34])=[O:17])[C:9]1=[O:37])=O)C.[K].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>O>[NH2:7][N:8]1[CH2:12][CH2:11][N:10]([C:13](=[O:36])[CH2:14][O:15][P:16]([OH:35])([N:18]2[C:21](=[O:22])[C@@H:20]([NH:23][C:24](=[O:33])[O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:19]2[CH3:34])=[O:17])[C:9]1=[O:37]

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 5462222PotassiumHCID 86741986(2S-trans)[1-[[2-[3-[[(1,1-Dimethylethoxy)-carbonyl]amino]-2-oxo-1-imidazolidinyl]-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

생성물 1

HCID 86741985(2S-trans)[1-[[2-(3-Amino-2-oxo-1-imidazolidinyl)-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

시약·촉매·용매 1

HCID 962Water용매

실험 절차

(2S-trans)[1-[[2-[3-[[(1,1-Dimethylethoxy)-carbonyl]amino]-2-oxo-1-imidazolidinyl]-2-oxoethoxy]hydroxyphosphinyl]-2-methyl-4-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester, monopotassium salt (5.9 g, 10 mmol) was treated at 0° C. sequentially with anisole (25 ml) and trifluoroacetic acid (60 ml), and the solution was stirred for six hours. The solution was evaporated in vacuo at ambient temperature and then co-evaporated with toluene (10 ml). The residue was triturated with hexane (50 ml) and diethyl ester (2×50 ml) to give a white solid. The solid was dissolved in water (10 ml) and the pH adjusted to 2.5 with sodium bicarbonate. This solution was chromatographed on a column of CHP20P reverse phase resin and eluted with an acetonitrile/water gradient. The appropriate fractions were combined and evaporated in vacuo to ~100 ml. This was lyophilized to give the title compound as a white solid, 2.520 g.

후처리

  1. customThe solution was evaporated in vacuo at ambient temperature
  2. customThe residue was triturated with hexane (50 ml) and diethyl ester (2×50 ml)
  3. customto give a white solid
  4. customThis solution was chromatographed on a column of CHP20P reverse phase resin
  5. washeluted with an acetonitrile/water gradient
  6. customevaporated in vacuo to ~100 ml

출처 및 근거

ORD 기록
ord-acf88472c2ef4cab9331b6f75454c6a6
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723002

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