Sodium borohydride → HCID 69202369, compound

HRID 2377265Notes

Reaction equation

HRID 2377265 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[N:10]2[C:14]3[C:15]4[C:20]([CH2:21][C:13]=3[C:12]([C:30]3[S:34][C:33]([CH:35]=[O:36])=[CH:32][CH:31]=3)=[N:11]2)=[CH:19][C:18]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:17][CH:16]=4)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO.O1CCCC1>[CH3:44][O:43][C:40]1[CH:41]=[CH:42][C:37]([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:10]2[C:14]3[C:15]4[C:20]([CH2:21][C:13]=3[C:12]([C:30]3[S:34][C:33]([CH2:35][OH:36])=[CH:32][CH:31]=3)=[N:11]2)=[CH:19][C:18]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[CH:17][CH:16]=4)=[CH:38][CH:39]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 87732437HCID 87732437, compound

Product 1

HCID 69202369HCID 69202369, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 331 (8.5 g, 14.1 mmol) in methanol (150 mL) and tetrahydrofuran (80 mL) was added sodium borohydride (530 mg, 14.1 mmol) at about 0° C. The mixture was stirred for about 3 hours while being allowed to warm to room temperature and was then concentrated under vacuum. The residue was diluted with water, extracted with ethyl acetate and the combined organic extracts were dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel using dichloromethane/methanol (10:1) as eluent to provide the desired product. MS (ESI): m/z 607 (M+H)+.

Workup

  1. concentrationwas then concentrated under vacuum
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-540ab2b8dfe646da8233d52df25f8386
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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