Borane;tetrahydrofuran → HCID 59778163, compound

HRID 1363100Notes

Reaction equation

HRID 1363100 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[CH2:11][C:10]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:29])=[O:28])([CH3:25])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[CH2:11][C:10]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)(=[O:29])=[O:28])([CH3:25])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 59778162HCID 59778162, compound

Product 1

HCID 59778163HCID 59778163, compoundYield 55%

Procedure

To compound 148H ((75 mg, 0.15 mmol) was added BH3THF (1M, 1.5 mL, 1.5 mmol) at RT under Argon. After addition, the reaction was stirred at RT for 24 h, then quenched by carefully adding MeOH (1 mL). The resulting mixture was stirred at RT for 2 h, then partitioned between saturated aqueous Na2CO3 (10 mL) and EtOAc. The aqueous layer was extracted with EtOAc (15 mL×3) and the combined EtOAc extracts washed with brine, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc (0-40%) in hexane to give the title compound as an off-white solid (40 mg, 55%). HPLC: 99% at 8.50 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient (A=90% H2O−110% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4), Flow rate at 2.5 mL/min, UV detection at 220 nm). MS (ES): m/z 487 [M+H]+.

Workup

  1. additionAfter addition
  2. customquenched by carefully adding MeOH (1 mL)
  3. stirringThe resulting mixture was stirred at RT for 2 h
  4. custompartitioned between saturated aqueous Na2CO3 (10 mL) and EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc (15 mL×3)
  6. washthe combined EtOAc extracts washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe resulting residue was chromatographed (silica gel)
  10. washeluting with EtOAc (0-40%) in hexane

Sources & evidence

ORD record
ord-285b18570c1c40b79968277401c9655b
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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