Trisodium Phosphate → Sodium (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethyl-thiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 1799702노트

반응식

HRID 1799702 반응식
P([O-])([O-])([O-])=O.[Na+:6].[Na+].[Na+].[OH:9][C@@H:10]([C@H:12]1[C:42](=[O:43])[N:14]2[C:15]([C:29]([O:31]CC3C=CC([N+]([O-])=O)=CC=3)=[O:30])=[C:16]([S:19]/[CH:20]=[CH:21]\[C:22]3[S:26][CH:25]=[N:24][C:23]=3[CH2:27][OH:28])[C@H:17]([CH3:18])[C@H:13]12)[CH3:11]>C1COCC1.[Pd]>[OH:9][C@@H:10]([C@H:12]1[C:42](=[O:43])[N:14]2[C:15]([C:29]([O-:31])=[O:30])=[C:16]([S:19]/[CH:20]=[CH:21]\[C:22]3[S:26][CH:25]=[N:24][C:23]=3[CH2:27][OH:28])[C@H:17]([CH3:18])[C@H:13]12)[CH3:11].[Na+:6]

참가 물질

5

반응물 2

HCID 24243Trisodium PhosphateHCID 694700964-Nitrobenzyl (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate

생성물 1

HCID 23676797Sodium (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethyl-thiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

10% Pd—C (hydrous, water content 53%) (1.42 g) was added to a solution of 40 ml of a 1/15 M sodium phosphate buffer solution (pH 6.8) of 957 mg of 4-nitrobenzyl (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate in 40 ml of THF, and the mixture was stirred under a hydrogen atmosphere for 1.5 hr. The 10% Pd—C was removed by filtration and was washed with water. The filtrate was adjusted to pH 6.6 by the addition of saturated sodium bicarbonate water, followed by washing with 40 ml of ethyl acetate. The aqueous layer was concentrated to about 5 ml, and the concentrate was purified by column chromatography (2% methanol-water) on Cosmosil 40C18-PREP to give 360 mg of the title compound.

후처리

  1. customThe 10% Pd—C was removed by filtration
  2. washwas washed with water
  3. additionThe filtrate was adjusted to pH 6.6 by the addition of saturated sodium bicarbonate water
  4. washby washing with 40 ml of ethyl acetate
  5. concentrationThe aqueous layer was concentrated to about 5 ml
  6. customthe concentrate was purified by column chromatography (2% methanol-water) on Cosmosil 40C18-PREP

출처 및 근거

ORD 기록
ord-dafaa43b2ab9471aa57a5cda563386e7
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344154B2

반응 노트

불러오는 중…