Sodium borohydride → HCID 117716498, compound

HRID 1396269Notes

Reaction equation

HRID 1396269 reaction equation
[CH2:1]([O:8][C@H:9]([C@H:12]1[O:20][C@H:19]2[C@H:15]([N:16]=[C:17]([N:21]([CH3:23])[CH3:22])[S:18]2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:13]1[O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O>[CH2:1]([O:8][C@@H:9]([C@@H:12]1[O:20][C@H:19]2[C@H:15]([N:16]=[C:17]([N:21]([CH3:23])[CH3:22])[S:18]2)[C@@H:14]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@@H:13]1[O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH:10]=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 87687587HCID 87687587, compound

Product 1

HCID 117716498HCID 117716498, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 98 (1.5 g, 2.7 mmol) (Prepared according to the synthesis of Example 149 and 150), step 6) was treated with NaBH4 (504 mg, 13 mmol) for 1 hour at 0° C. The resulting solution was diluted with H2O (60 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give a residue, which was purified by silica gel column, eluted with 20%-50% ethyl acetate in petroleum ether to give 102 as brown syrup (1.2 g, 80%); (ES, m/z): [M+H]+ 549.1; 1H NMR (300 MHz, CDCl3) δ 7.22-7.45 (m, 15H), 6.35 (d, J=6.9 Hz, 1H), 4.61-4.80 (m, 4H), 4.47-4.53 (m, 2H), 4.25-4.36 (m, 1H), 4.08-4.12 (m, 1H), 3.89-3.92 (m, 1H), 3.46-3.78 (m, 4H), 3.01 (s, 6H).

Workup

  1. customaccording to the synthesis of Example 149 and 150), step 6)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue, which
  7. customwas purified by silica gel column
  8. washeluted with 20%-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-98f62318faf443e286d49165e4e53190
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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