Sodium borohydride → HCID 68866288, compound

HRID 1725884Notes

Reaction equation

HRID 1725884 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH2:18][CH2:17][CH2:16][C:15](=[O:22])[C:14]=3[C:13]=2[C:23]([OH:25])=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH2:18][CH2:17][CH2:16][CH:15]([OH:22])[C:14]=3[C:13]=2[C:23]([OH:25])=[O:24])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68864168HCID 68864168, compound

Product 1

HCID 68866288HCID 68866288, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 103B (25 mg, 0.068 mmol) in methanol (3 mL) was treated with NaBH4 (5.2 mg, 0.137 mmol), stirred at room temperature for 3 hours, and concentrated. The concentrate was purified by reverse phase HPLC to provide the desired product. MS (ESI) m/e 364 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 7.74 (m, 2H), 7.32 (m, 2H), 7.23 (d, 1H), 7.18 (br s, 1H), 6.9 (d, 1H), 4.59 (br s, 1H), 2.6 (m, 2H), 1.85 (m, 2H), 1.5 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-fad9032c9aa046f580a23996fd015386
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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