Sodium borohydride → HCID 178477658, compound

HRID 930894Notes

Reaction equation

HRID 930894 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:23][CH:24]2[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]2)=[C:10]([C:12]2[C:13]3[CH:22]=[CH:21][NH:20][C:14]=3[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)[CH:11]=1)(=[O:5])=[O:4])[CH3:2].[BH4-].[Na+]>O1CCCC1>[CH2:1]([S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:23][C@H:24]2[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26][CH2:25]2)=[C:10]([C:12]2[C:13]3[CH:22]=[CH:21][NH:20][C:14]=3[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)[CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89656275HCID 89656275, compound

Product 1

HCID 178477658HCID 178477658, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 199 (0.052 g, 0.121 mmol) and sodium tetrahydroborate (6.89 mg, 0.182 mmol) in tetrahydrofuran (5 mL) was heated at 60° C. for 2 hours. The solvent was removed, and the solid was treated with MeOH and a couple of drops of TFA. The resulting solution was purified by Preparative HPLC (C18, 10-80% CH3CN/water (0.1% TFA)) to give the title compound (second eluting peak, 0.036 g, 0.084 mmol, 68.9% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.06 (s, 1H), 7.78-7.82 (m, 2H), 7.36-7.38 (m, 2H), 7.30 (t, J=2.75 Hz, 1H), 6.14-6.16 (m, 1H), 4.62-4.63 (m, 1H), 3.51-3.58 (m, 5H), 3.25-3.31 (m, 2H), 1.75-1.81 (m, 2H), 1.50-1.64 (m, 4H), 1.32-1.40 (m, 2H), 1.14 (t, J=7.32 Hz, 3H). MS (ESI+) m/z 431.2 (M+H)+.

Workup

  1. customThe solvent was removed
  2. additionthe solid was treated with MeOH and a couple of drops of TFA
  3. customThe resulting solution was purified by Preparative HPLC (C18, 10-80% CH3CN/water (0.1% TFA))

Sources & evidence

ORD record
ord-e8713b9bedd249729c15381ff95d4aa5
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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