Water → HCID 89823611, compound

HRID 1400076Notes

Reaction equation

HRID 1400076 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]([C@@:17]12[CH2:24][CH2:23][CH2:22][C@@H:21]1[CH2:20][C@@H:19]([N:25](C(=O)C(F)(F)F)[C@@H:26]1[C@H:31]([O:32][CH3:33])[CH2:30][O:29][CH2:28][CH2:27]1)[CH2:18]2)=[O:16])=[O:7])(C)(C)C.[BH4-].[Na+].O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl.C(O)C>[C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]([C@@:17]12[CH2:24][CH2:23][CH2:22][C@@H:21]1[CH2:20][C@@H:19]([NH:25][C@@H:26]1[C@H:31]([O:32][CH3:33])[CH2:30][O:29][CH2:28][CH2:27]1)[CH2:18]2)=[O:16])([OH:7])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 89823596HCID 89823596, compound

Product 1

HCID 89823611HCID 89823611, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

A solution of Example 11A (5.5 g, 9.8 mmol) and NaBH4 (1.1 g, 29.4 mmol) in dichloromethane/ethanol (20 mL/20 mL) was stirred at room temperature for 2 hours. Water was added and the resulting solution was adjusted to pH=10 with saturated Na2CO3 solution and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated to result in the title compound (4.3 g, 95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4e53808cf33541bb954505685cb800c9
Source dataset
uspto-grants-2014_12
Patent number
US08906911B2

Reaction notes

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