Potassium Acetate → (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carboxylic acid

HRID 422168노트

반응식

HRID 422168 반응식
FC(F)(F)S(OC1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]2[C:8]=1[C@@:9]1([CH3:30])[C@H:18]([CH2:19][S:20]2)[C@:17]2([CH3:27])[C@H:12]([C:13]([CH3:29])([CH3:28])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]1)(=O)=O.[CH3:33][C:34]([O-:36])=[O:35].[K+]>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C(Cl)Cl>[CH3:26][O:25][C:23]1[CH:22]=[C:21]2[C:8]([C@@:9]3([CH3:30])[C@H:18]([CH2:19][S:20]2)[C@:17]2([CH3:27])[C@H:12]([C:13]([CH3:29])([CH3:28])[CH2:14][CH2:15][CH2:16]2)[CH2:11][CH2:10]3)=[C:33]([C:34]([OH:36])=[O:35])[CH:24]=1

참가 물질

6

반응물 2

HCID 517044Potassium AcetateHCID 53241983(1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl trifluoromethanesulfonate

생성물 1

HCID 58294803(1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carboxylic acid수율 34.3%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178478483HCID 178478483, 화합물촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

A mixture of (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-yl trifluoromethanesulfonate (32) (1.5 g, 3.0 mmol), KOAc (1.1 g, 12 mmol), Pd(OAc)2 (0.3 g, 2 mmol), dppf:CH2Cl2 1:1 (0.97 g, 1.3 mmol) was prepared in DMSO (15 mL) and purged with N2. The reaction mixture was subjected to carbon monoxide via a balloon. The mixture was stirred at 60° C. for 18 h. The reaction was cooled to room temperature and quenched with water, acidified with 1 M HCl and extracted with EtOAc. The organic layer was concentrated to dryness. The crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 1:1) to yield (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carboxylic acid (74) (0.40 g, 34%) as a brown solid.

후처리

  1. custompurged with N2
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with water
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated to dryness
  6. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/EtOAc, 1:1)

출처 및 근거

ORD 기록
ord-55a8882ac3d34ab5a65f1a463815a4ed
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101605B2

반응 노트

불러오는 중…