反应 #48628

ord-29601f73a49241d690cf70d5de7a0301

反应方程式

O
water
CC(C)(C)OC(=O)N1[C@@H]([C@@H](OCc2ccccc2)[C@H](Cc2cccc(OCc3ccccc3)c2)N(Cc2ccccc2)Cc2ccccc2)COC1(C)C
4-(R)-[1-(S)-benzyloxy-3-(3-benzyloxyphenyl)-2-(S)-dibenzylaminopropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
O
water
O=C([O-])O.[Na+]
sodium bicarbonate
→
N[C@H](CO)[C@@H](OCc1ccccc1)[C@H](Cc1cccc(OCc2ccccc2)c1)N(Cc1ccccc1)Cc1ccccc1
crude desired compound
N[C@H](CO)[C@@H](OCc1ccccc1)[C@H](Cc1cccc(OCc2ccccc2)c1)N(Cc1ccccc1)Cc1ccccc1
2-(R)-Amino-3-(R)-benzyloxy-5-(3-benzyloxyphenyl)-4-(S)-dibenzylaminopentan-1-ol

反应物

O
water
CC(C)(C)OC(=O)N1[C@@H]([C@@H](OCc2ccccc2)[C@H](Cc2cccc(OCc3ccccc3)c2)N(Cc2ccccc2)Cc2ccccc2)COC1(C)C
4-(R)-[1-(S)-benzyloxy-3-(3-benzyloxyphenyl)-2-(S)-dibenzylaminopropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
O
water
O=C([O-])O.[Na+]
sodium bicarbonate

试剂

无

溶剂

Cl
hydrogen chloride
C1COCCO1
1,4-dioxane

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取Extract with ethyl acetate
  2. 2
    洗涤wash with saturated aqueous sodium chloride
  3. 3
    干燥dry (magnesium sulfate)
  4. 4
    过滤filter
  5. 5
    浓缩concentrate

实验过程

Dissolve 4-(R)-[1-(S)-benzyloxy-3-(3-benzyloxyphenyl)-2-(S)-dibenzylaminopropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (16.01 g, 22.0 mmol) in 4 M hydrogen chloride in 1,4-dioxane (130 mL) and stir for 30 minutes. Add water (65 mL) and stir for 18 hours. Slowly add sodium bicarbonate (50 g) and water (˜50 mL). Extract with ethyl acetate, wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate to give the crude desired compound.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07745438B2uspto-grants-2010_06