醋酸 → HCID 178516684，化合物

HRID 1160255

反应方程式

HRID 1160255 反应方程式
C([C@@H]1CO[C:10](=O)[N:9]1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[Cl:35])[CH2:16]C=O)C1C=CC=CC=1.N[C@H:38]1[CH2:43][CH2:42][C@H:41]([OH:44])[CH2:40][CH2:39]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>ClCCCl>[CH2:28]([O:27][C:23]1[CH:22]=[C:21]([Cl:35])[C:20]([CH2:19][C@@H:15]2[CH2:16][CH2:10][N:9]([C@H:38]3[CH2:43][CH2:42][C@H:41]([OH:44])[CH2:40][CH2:39]3)[C:14]2=[O:36])=[C:25]([Cl:26])[CH:24]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参与物

6

反应物 4

HCID 176醋酸HCID 5049666三乙酰氧基硼氢化钠HCID 59515429(R)-4-((R)-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehydeHCID 178511715HCID 178511715，化合物

产物 1

HCID 178516684HCID 178516684，化合物

试剂、催化剂与溶剂 1

HCID 111,2-二氯乙烷溶剂

实验过程

Mix (R)-4-((R)-4-benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dichloro-benzyl)-4-oxo-butyraldehyde (Preparation 10) (3.054 g, 5.8 mmol), trans-4-amino-cyclohexanol (1.35, 11.6 mmol), NaBH(OAc)3 (5.18 g, 23.21 mmol) and acetic acid (0.63 mL, 11.2 mmol) in 50 mL of 1,2-dichloroethane. Stir for 12 hours at room temperature. Quench with saturated solution of NaHCO3 and extract with ethyl acetate. Wash the extract with brine. Dry over magnesium sulfate, filter, and concentrate. After flash column chromatography receive 1.39 g (54%) of the title compound: Mass spectrum (apci) m/z=448 (M+H).

后处理

  1. customQuench with saturated solution of NaHCO3
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with brine
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

来源与证据

ORD记录
ord-da756b63c838490588894d2604175168
来源数据集
uspto-grants-2010_10
专利号
US07816349B2

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