Hydrochloric Acid → HCID 71459160, 화합물

HRID 1429762노트

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HRID 1429762 반응식
[CH3:1][CH2:2][C:3]1[CH2:23][N:21]2[CH2:22][C@@H:5]([CH2:6][C@:7]([C:57]([O:59][CH3:60])=[O:58])([C:24]3[CH:25]=[C:26]4[C@:34]56[C@@H:38]7[C@:39]([CH2:54][CH3:55])([C@@H:43]([O:50][C:51]([CH3:53])=[O:52])[C@:44]([OH:49])([C:45]([O:47][CH3:48])=[O:46])[C@@H:33]5[N:32]([CH3:56])[C:27]4=[CH:28][C:29]=3[O:30][CH3:31])[CH:40]=[CH:41][CH2:42][N:37]7[CH2:36][CH2:35]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][C:12]([O:17][CH3:18])=[CH:11][C:10]=4[C:9]=3[CH2:19][CH2:20]2)[CH:4]=1.Cl.C(C[OH:67])(F)(F)F.[BH4-].[Na+]>O.O.O.O.O.O.O.C([O-])(=O)C([O-])=O.[Fe+3].C([O-])(=O)C([O-])=O.C([O-])(=O)C([O-])=O.[Fe+3].CCOC(C)=O.CO.CCN(CC)CC>[CH3:1][CH2:2][C@@:3]1([OH:67])[CH2:23][N:21]2[CH2:22][C@@H:5]([CH2:6][C@:7]([C:57]([O:59][CH3:60])=[O:58])([C:24]3[CH:25]=[C:26]4[C@:34]56[C@@H:38]7[C@:39]([CH2:54][CH3:55])([C@@H:43]([O:50][C:51]([CH3:53])=[O:52])[C@:44]([OH:49])([C:45]([O:47][CH3:48])=[O:46])[C@@H:33]5[N:32]([CH3:56])[C:27]4=[CH:28][C:29]=3[O:30][CH3:31])[CH:40]=[CH:41][CH2:42][N:37]7[CH2:36][CH2:35]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][C:12]([O:17][CH3:18])=[CH:11][C:10]=4[C:9]=3[CH2:19][CH2:20]2)[CH2:4]1

참가 물질

10

반응물 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 4311764Sodium borohydrideHCID 71450167HCID 71450167, 화합물

생성물 1

HCID 71459160HCID 71459160, 화합물수율 48%

시약·촉매·용매 5

HCID 57370413Iron(3+) ethanedioate--water (2/3/6)촉매HCID 887Methanol용매HCID 962Water용매3회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A mixture of iron(III) oxalate hexahydrate (79.4 mg, 0.13 mmol, 30 equiv) in H2O (22 mL) was cooled to 0° C. and air was bubbled through the mixture for 10 minutes. A solution of 10′-methoxyanhydro-vinblastine (22a, 4.5 mg, 0.0055 mmol, 1 equiv) in H2O (0.5 mL), aqueous 0.1 N HCl (0.5 mL), and CF3CH2OH (0.1 mL) was transferred by pipette to the mixture and NaBH4 (4.1 mg, 0.11 mmol, 20 equiv) in H2O (1 mL) was added to the mixture at 0° C. The resulting mixture was stirred for 30 min before being quenched by addition of 28-30% aqueous NH4OH (10 mL). The mixture was extracted with 10% MeOH in CH2Cl2 and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. PTLC (SiO2, Et3N:MeOH:EtOAc=3:3:97) provided 10′-methoxyvinblastine (22b, 2.2 mg, 0.0026 mmol, 48%) as a white solid and 10′-methoxyleurosidine (1.3 mg, 0.0015 mmol, 28%).

후처리

  1. customair was bubbled through the mixture for 10 minutes
  2. additionwas added to the mixture at 0° C
  3. custombefore being quenched by addition of 28-30% aqueous NH4OH (10 mL)
  4. extractionThe mixture was extracted with 10% MeOH in CH2Cl2
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-67c1e353b31b4c1c81858fa06e0f5daf
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940754B2

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