Tetrahydrofuran → HCID 68311055, compound

HRID 470673Notes

Reaction equation

HRID 470673 reaction equation
[BH4-].[Li+].O1CCCC1.[Cl:8][C:9]1[CH:17]=[C:16]2[C:12]([C@@:13]3([C@@H:22]([C:23]4[CH:28]=[C:27]([C:29](OC)=[O:30])[CH:26]=[C:25]([Cl:33])[CH:24]=4)[C@H:21]([C:34]([NH:36][C@@H:37]4[CH2:42][CH2:41][C@@H:40]([CH2:43][OH:44])[O:39][CH2:38]4)=[O:35])[NH:20][C:19]43[CH2:49][CH2:48][C:47]([CH3:51])([CH3:50])[CH2:46][CH2:45]4)[C:14](=[O:18])[NH:15]2)=[CH:11][CH:10]=1>O>[Cl:8][C:9]1[CH:17]=[C:16]2[C:12]([C@@:13]3([C@@H:22]([C:23]4[CH:28]=[C:27]([CH2:29][OH:30])[CH:26]=[C:25]([Cl:33])[CH:24]=4)[C@H:21]([C:34]([NH:36][C@@H:37]4[CH2:42][CH2:41][C@@H:40]([CH2:43][OH:44])[O:39][CH2:38]4)=[O:35])[NH:20][C:19]43[CH2:49][CH2:48][C:47]([CH3:51])([CH3:50])[CH2:46][CH2:45]4)[C:14](=[O:18])[NH:15]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 68310721HCID 68310721, compound

Product 1

HCID 68311055HCID 68311055, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium borohydride (26 mg, 1.25 mmol) was gradually added to a tetrahydrofuran (4 ml) solution of the compound (107 mg, 0.17 mmol) obtained in Step 2 of Example 22 at room temperature and the resulting mixture was stirred at the same temperature for 18 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and then the residue was purified by silica gel column chromatography [methanol:ethyl acetate=1:9 (v/v)] to give 69 mg (68%) of the title compound as a colorless solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [methanol:ethyl acetate=1:9 (v/v)]

Sources & evidence

ORD record
ord-d6c889dbaa374ec7b66cc15ec90f0914
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

Loading…