Hydrochloric Acid → HCID 71455533、化合物

HRID 1429758ノート

反応式

HRID 1429758 の反応式
[CH3:1][CH2:2][C:3]1[CH2:22][N:20]2[CH2:21][C@@H:5]([CH2:6][C@:7]([C:56]([O:58][CH3:59])=[O:57])([C:23]3[CH:24]=[C:25]4[C@:33]56[C@@H:37]7[C@:38]([CH2:53][CH3:54])([C@@H:42]([O:49][C:50]([CH3:52])=[O:51])[C@:43]([OH:48])([C:44]([O:46][CH3:47])=[O:45])[C@@H:32]5[N:31]([CH3:55])[C:26]4=[CH:27][C:28]=3[O:29][CH3:30])[CH:39]=[CH:40][CH2:41][N:36]7[CH2:35][CH2:34]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][C:12]([Cl:17])=[CH:11][C:10]=4[C:9]=3[CH2:18][CH2:19]2)[CH:4]=1.Cl.C(C[OH:66])(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:66])[CH2:22][N:20]2[CH2:21][C@@H:5]([CH2:6][C@:7]([C:56]([O:58][CH3:59])=[O:57])([C:23]3[CH:24]=[C:25]4[C@:33]56[C@@H:37]7[C@:38]([CH2:53][CH3:54])([C@@H:42]([O:49][C:50]([CH3:52])=[O:51])[C@:43]([OH:48])([C:44]([O:46][CH3:47])=[O:45])[C@@H:32]5[N:31]([CH3:55])[C:26]4=[CH:27][C:28]=3[O:29][CH3:30])[CH:39]=[CH:40][CH2:41][N:36]7[CH2:35][CH2:34]6)[C:8]3[NH:16][C:15]4[CH:14]=[CH:13][C:12]([Cl:17])=[CH:11][C:10]=4[C:9]=3[CH2:18][CH2:19]2)[CH2:4]1

参加物

10

反応物 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 4311764Sodium borohydrideHCID 71453801HCID 71453801、化合物

生成物 1

HCID 71455533HCID 71455533、化合物収率 42%

試薬・触媒・溶媒 5

HCID 57370413Iron(3+) ethanedioate--water (2/3/6)触媒HCID 887Methanol溶媒HCID 962Water溶媒3 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A mixture of iron(III) oxalate hexahydrate (52.6 mg, 0.109 mmol, 30 equiv) in H2O was cooled to 0° C. and air was bubbled through the mixture for 10 minutes. A solution of 10′-chloroanhydrovinblastine (18a, 3.0 mg, 0.0036 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 (2.7 mg, 0.073 mmol, 20 equiv) in H2O (1 mL) was added to the mixture at 0° C. The resulting mixture was stirred for 30 minutes 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′-chlorovinblastine (18b, 1.3 mg, 0.0015 mmol, 42%) as a white solid and 10′-chloroleurosidine (0.8 mg, 0.00095 mmol, 26%).

後処理

  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

出典と根拠

ORDレコード
ord-89e8745b45e64932ac63da7cafb28491
出典データセット
uspto-grants-2015_01
特許番号
US08940754B2

反応ノート

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