Acetic Acid → HCID 86697142, compound

HRID 237478Notes

Reaction equation

HRID 237478 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][C:5]([CH3:43])([CH:41]=O)[CH2:6][O:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]3[C:16]=2[CH2:17][CH2:18][C@H:19]3[O:25][C:26]2[CH:39]=[CH:38][C:29]3[C@H:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH2:31][O:32][C:28]=3[CH:27]=2)=[C:10]([CH3:40])[CH:9]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.ClCCCl.ClCCl>[CH3:1][N:2]([CH3:3])[CH2:41][C:5]([CH3:43])([CH3:4])[CH2:6][O:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]3[C:16]=2[CH2:17][CH2:18][C@H:19]3[O:25][C:26]2[CH:39]=[CH:38][C:29]3[C@H:30]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH2:31][O:32][C:28]=3[CH:27]=2)=[C:10]([CH3:40])[CH:9]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86697143HCID 86697143, compound

Product 1

HCID 86697142HCID 86697142, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (95 μL of a 2 M solution in tetrahydrofuran) is added to a solution of methyl 2-((S)-6-((R)-4-(4-(2,2-dimethyl-3-oxopropoxy)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (83 mg) and acetic acid (13 μL) in 1,2-dichloroethane (2 mL). The mixture is stirred for 20 minutes and then treated with sodium triacetoxyborohydride (130 mg). After stirring for 12 hours the mixture is diluted with dichloromethane, washed with water and brine, dried (MgSO4) and concentrated. The residue is purified by HPLC on reversed phase to give the title compound. Yield: 20 mg; LC (method 13): tR=1.18 min; Mass spectrum (ESI+): m/z=576 [M+H]+.

Workup

  1. stirringAfter stirring for 12 hours the mixture
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is purified by HPLC on reversed phase

Sources & evidence

ORD record
ord-175ace7e9a5f453ebad7f0ec70fb6102
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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