Acetic Acid → HCID 59775207, compound

HRID 1361067Notes

Reaction equation

HRID 1361067 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:28])[C@H:15]([O:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:16][CH:17]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][NH:39][CH3:40])=[CH:32][C:31]=1[CH3:41].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:28])[C@H:15]([O:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:16][CH2:17][N:39]([CH2:38][CH2:37][CH2:36][C:33]1[CH:34]=[CH:35][C:30]([F:29])=[C:31]([CH3:41])[CH:32]=1)[CH3:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 59775184HCID 59775184, compoundHCID 59775197HCID 59775197, compound

Product 1

HCID 59775207HCID 59775207, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (R)-4-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-(4-fluoro-3-methylphenoxy)-4-oxobutanal (35 mg, 0.091 mmol) in 3 mL DCE was added 3-(4-Fluoro-3-methylphenyl)-N-methylpropan-1-amine (22 mg, 0.12 mmol) followed by NaBH(OAc)3 (29.5 mg, 0.14 mmol) and AcOH (7.2 mg, 0.12 mmol) at room temperature. The mixture was stirred for 8 h at the room temperature. The reaction was quenched by pouring into 10 mL 5% aqueous NaOH and diluted with ethyl acetate. The mixture was extracted with more ethyl acetate (3×15 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product used directly in the next step without further purification.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into 10 mL 5% aqueous NaOH
  3. additiondiluted with ethyl acetate
  4. extractionThe mixture was extracted with more ethyl acetate (3×15 mL)
  5. washthe combined organic layers washed with brine (2×10 mL)
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed under reduced pressure
  8. customthe crude product used directly in the next step without further purification

Sources & evidence

ORD record
ord-5c287d79792a4b28972e9e3f9e4cc607
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

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