Acetic Acid → HCID 89814159, compound

HRID 525365Notes

Reaction equation

HRID 525365 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][C:10]1([CH3:29])[O:14][C:13](=[O:15])[N:12]([CH:16]2[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]2)[C@H:11]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.ClCCCl>[I:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][CH:19]1[CH2:18][CH2:17][CH:16]([N:12]2[C@@H:11]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:10]([CH3:9])([CH3:29])[O:14][C:13]2=[O:15])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 119952-IodoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 89813764HCID 89813764, compound

Product 1

HCID 89814159HCID 89814159, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

The starting material (see Intermediate M synthesis) was a mixture of S:R stereoisomers (˜3:1). To a vial charged with 2-iodoaniline (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (0.100 g, 0.457 mmol) were added (S)-5,5-dimethyl-3-(4-oxocyclohexyl)-4-phenyloxazolidin-2-one (0.131 g, 0.457 mmol), DCE (1.826 mL) and AcOH (0.039 mL, 0.685 mmol). The mixture was stirred at room temperature for 15 minutes prior to the addition of sodium triacetoxyborohydride (0.213 g, 1.004 mmol). The pale yellow suspension was then stirred overnight at room temperature. Water was added to the mixture and the resulting mixture was transferred to a separatory funnel and extracted with DCM (2×). The combined organic layers were dried with Na2SO4, filtered, and dried under reduced pressure. The material thus obtained was purified with a 25 g SNAP column (Biotage) ramping EtOAc in heptane (10% DCM throughout, 0-50%) providing the desired product as a mixture of isomers according to LC-MS (2:1 cis:trans). m/z (ESI) 491.1 (M+H)+.

Workup

  1. additiona mixture of S
  2. stirringThe pale yellow suspension was then stirred overnight at room temperature
  3. customthe resulting mixture was transferred to a separatory funnel
  4. extractionextracted with DCM (2×)
  5. dry with materialThe combined organic layers were dried with Na2SO4
  6. filtrationfiltered
  7. customdried under reduced pressure
  8. customThe material thus obtained
  9. customwas purified with a 25 g SNAP column (Biotage)

Sources & evidence

ORD record
ord-7fbe7a6fe751426588d912890e4f7881
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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