Dimethyl Sulfoxide → (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde

HRID 1913052노트

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HRID 1913052 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C@H:19]1[C@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@@:22]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([CH2:50][C:51]3[CH:56]=[CH:55][C:54]([O:57][CH2:58][C:59]([F:62])([F:61])[F:60])=[CH:53][CH:52]=3)[CH:44]=2)([O:41][CH3:42])[O:21][C@@H:20]1[CH2:63][OH:64])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C@H:19]1[C@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:23]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@@:22]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([CH2:50][C:51]3[CH:52]=[CH:53][C:54]([O:57][CH2:58][C:59]([F:61])([F:62])[F:60])=[CH:55][CH:56]=3)[CH:44]=2)([O:41][CH3:42])[O:21][C@@H:20]1[CH:63]=[O:64])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68015082[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol

생성물 1

HCID 86685150(2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde수율 96.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

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온도
-78 °C

실험 절차

Oxalyl chloride (0.16 mL, 1.87 mmol) was dissolved in 5 mL dichloromethane and cooled to −78° C., followed by dropwise addition of dimethyl sulfoxide (0.2 mL, 2.88 mmol) in dichloromethane (3 mL). The reaction mixture was stirred for 15 minutes, before 10 mL solution of [(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methanol 7h (1.10 g, 1.44 mmol) in dichloromethane were added and stirred for 40 minutes. Then the reaction mixture was warmed and stirred for 3 hours at room temperature after triethylamine (1.0 mL, 7.21 mmol) was dropwise added. Thereafter, the reaction mixture was partitioned after 5 mL 1 M hydrochloric acid were added, the aqueous phase was extracted with ethyl acetate (10 mL×2) and the organic extracts were combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (2S,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-carbaldehyde 7i (1.06 g, yellow grease), which was used directly in the next step without purification.

후처리

  1. additionwere added
  2. temperatureThen the reaction mixture was warmed
  3. additionwas dropwise added
  4. customThereafter, the reaction mixture was partitioned after 5 mL 1 M hydrochloric acid
  5. additionwere added
  6. extractionthe aqueous phase was extracted with ethyl acetate (10 mL×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5633a965df7848c1965c468db918c3fc
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609622B2

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