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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Hydrochloric Acid → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(5-oxo-2H-furan-3-yl)sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 467371
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HRID 467371 반응식
[O:1]=[C:2]1[CH:6]=[C:5]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[C@H:32]([NH:33][C:34](=[O:82])/[C:35](/[C:57]4[N:58]=[C:59]([NH:62]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[S:60][CH:61]=4)=[N:36]\[O:37]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:31](=[O:83])[N:13]3[C:14]=2[C:15]([O:17]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:16])[CH2:4][O:3]1.Cl.O>C(O)=O>[NH2:62][C:59]1[S:60][CH:61]=[C:57](/[C:35](=[N:36]/[OH:37])/[C:34]([NH:33][C@@H:32]2[C:31](=[O:83])[N:13]3[C:14]([C:15]([OH:17])=[O:16])=[C:9]([CH2:8][S:7][C:5]4[CH2:4][O:3][C:2](=[O:1])[CH:6]=4)[CH2:10][S:11][C@H:12]23)=[O:82])[N:58]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 962WaterHCID 141558982benzhydryl (6R,7R)-8-oxo-3-[(5-oxo-2H-furan-3-yl)sulfanylmethyl]-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

생성물 1

HCID 88501503(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(5-oxo-2H-furan-3-yl)sulfanylmethyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
수율 39.7%

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

Diphenylmethyl 3-(2,5-dihydro-2-oxofuran-4-ylthiomethyl)-7β-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetamido]ceph-3-em-4-carboxylate (744 mg) was dissolved in 98-100% formic acid (13 ml) and 1N hydrochloric acid (0.65 ml) and water (0.65 ml) were added. The mixture was stirred at room temperature for 30 mins and then concentrated hydrochloric acid (0.52 ml) was added. After stirring for a further hour the solvents were removed on a rotary evaporator. A mixture of toluene and tetrahydrofuran was evaporated from the residue twice, and the residue triturated with ether. The solid was filtered off, and washed with ether. The solid was suspended in water and the pH adjusted to 2.6 with 0.1N sodium hydroxide, the mixture was stirred for a further 30 mins, occasionally adjusting the pH to 2.6. The solid was then filtered off, washed with cold water and dried under vacuum to give the title compound (128 mg) as an off-white solid. υmax (KBr) 1773, 1735, 1670, and 1629cm-1. δH [(CD3)2SO] 3.49 (1H, d, J 18.0Hz), 3.72 (1H, d, J 18.1Hz), 4.10 (1H, d, J 13.2Hz), 4.18 (1H, d, J 13.2Hz), 4.97 (2H, s), 5.18 (1H, d, J 4.8Hz), 5.79 (1H, dd, J 4.8 and 8.0Hz), 6.11 (1H, s), 6.67 (1H, s), 9.51 (1H, d, J 8.1Hz), 11.40 (1H, s). [mass spectrum: +ve ion (thioglycerol) MH+ 498].

후처리

  1. stirringAfter stirring for a further hour the solvents
  2. customwere removed on a rotary evaporator
  3. additionA mixture of toluene and tetrahydrofuran
  4. customwas evaporated from the residue twice
  5. customthe residue triturated with ether
  6. filtrationThe solid was filtered off
  7. washwashed with ether
  8. stirringthe mixture was stirred for a further 30 mins
  9. filtrationThe solid was then filtered off
  10. washwashed with cold water
  11. customdried under vacuum

출처 및 근거

ORD 기록
ord-8f343f9f13d44bc782027e0b918f7261
출처 데이터셋
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05158946

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