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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine → (R)-1-[2-Hydroxy-3-(2-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut1-enylamino)benzoyl]pyrrolidine-2-carboxylic acid

HRID 1528161
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HRID 1528161 반응식
[CH3:1][C:2]1[O:6][C:5]([CH:7]([NH2:13])[C:8]2([CH3:12])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C([O:16][C:17]1[C:20](=[O:21])[C:19](=O)[C:18]=1[NH:23][C:24]1[C:25]([OH:40])=[C:26]([CH:37]=[CH:38][CH:39]=1)[C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@@H:30]1[C:34]([OH:36])=[O:35])=[O:28])C>CO.C(OCC)C>[OH:40][C:25]1[C:24]([NH:23][C:18]2[C:17](=[O:16])[C:20](=[O:21])[C:19]=2[NH:13][CH:7]([C:5]2[O:6][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:8]2([CH3:12])[CH2:9][O:10][CH2:11]2)=[CH:39][CH:38]=[CH:37][C:26]=1[C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@@H:30]1[C:34]([OH:36])=[O:35])=[O:28]
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참가 물질

5

반응물 2

HCID 89525357C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine2회HCID 89534485(R)-1-[3-(2-Ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxybenzoyl]pyrrolidine-2-carboxylic acid

생성물 1

HCID 71555296(R)-1-[2-Hydroxy-3-(2-{[(5-methylfuran-2-yl)-(3-methyloxetan-3-yl)methyl]amino}-3,4-dioxocyclobut1-enylamino)benzoyl]pyrrolidine-2-carboxylic acid수율 58.6%

시약·촉매·용매 2

HCID 887
Methanol
용매
2회
HCID 3283Diethyl Ether용매

실험 절차

494 mg (2.73 mmol) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine in 3 ml of methanol were added to a solution of 500 mg (1.34 mmol) of (R)-1-[3-(2-ethoxy-3,4-dioxocyclobut-1-enylamino)-2-hydroxy-benzoyl]pyrrolidine-2-carboxylic acid in 47 ml of methanol at 50° C. After 3 days, 248 mg (1.37 mmol) of C-(5-methylfuran-2-yl)-C-(3-methyloxetan-3-yl)methylamine were added. After 4 days, the reaction medium was concentrated to dryness. The reaction medium was taken up in ethyl acetate and was washed with a saturated aqueous ammonium chloride solution and then with a 1 M aqueous solution of sodium dihydrogen phosphate. The organic phase was dried over magnesium sulfate, filtered and concentrated. The solid obtained was taken up, with stirring, in diethyl ether and a little ethyl acetate and was filtered. 400 mg of a beige solid were obtained. This solid was chromatographed on silica gel (ethyl acetate/acetone/water: 50/50/2 then 50/50/5). 240 mg were obtained in the form of a beige solid. Yield=35%, HPLC=52.43%+45.15% (mixture of the two diastereoisomers), Mp=198-205° C.

후처리

  1. waitAfter 4 days
  2. concentrationthe reaction medium was concentrated to dryness
  3. washwas washed with a saturated aqueous ammonium chloride solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solid obtained
  8. filtrationa little ethyl acetate and was filtered

출처 및 근거

ORD 기록
ord-c4dd62464bd349e484661227cfd6f189
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090596B2

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