HCID 118324862, compound → HCID 118324751, compound

HRID 587868Notes

Reaction equation

HRID 587868 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([C@@H:22]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([F:34])=[CH:26][CH:25]=1)[CH3:23])[CH2:8][CH2:9][CH2:10][C@H:11]1[CH2:20][CH:19]([OH:21])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)([CH3:4])([CH3:3])[CH3:2].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>>[C:1]([O:5][C:6](=[O:35])[N:7]([C@@H:22]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([F:34])=[CH:26][CH:25]=1)[CH3:23])[CH2:8][CH2:9][CH2:10][C@H:11]1[CH2:20][C:19](=[O:21])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 118324862HCID 118324862, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 118324751HCID 118324751, compoundYield 56.7%

Conditions

Temperature
25 °C

Procedure

To a stirred solution of tert-Butyl((R)-1-(4-fluoronaphthalen-1-yl)ethyl)(3-((2R)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)propyl)carbamate (886 mg, 1.855 mmol) DCM (8 mL), PCC (304 mg, 2.226 mmol) was added at 0° C. and stirred for 1 h at 25° C. The reaction mixture was filtered through celite bed and the filtrate concentrated to get the crude compound. This crude compound was purified by column chromatography (Biotage) using eluent (1:9, ethyl acetate:n-hexane) to get the title compound (500 mg). m/z 476.42.

Workup

  1. filtrationThe reaction mixture was filtered through celite bed
  2. concentrationthe filtrate concentrated
  3. customto get the crude compound
  4. customThis crude compound was purified by column chromatography (Biotage)

Sources & evidence

ORD record
ord-7f46d73048e042d7bdde1bdb26dcc53b
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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