Acetic Acid → HCID 68929051, compound

HRID 32117Notes

Reaction equation

HRID 32117 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH:14][C:15](=[O:39])[CH2:16][CH:17]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[NH:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)(=[O:21])=[O:20])[CH2:9][CH2:8][CH2:7]2)(=O)[CH3:2].[CH2:40]([NH2:44])[CH:41]([CH3:43])[CH3:42].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[F:38][C:35]1[CH:36]=[CH:37][C:32]([CH:17]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:29])[F:31])[CH:23]=2)(=[O:21])=[O:20])[CH2:16][C:15]([NH:14][CH:10]2[C:11]3[C:6](=[CH:5][C:4]([CH:1]([NH:44][CH2:40][CH:41]([CH3:43])[CH3:42])[CH3:2])=[CH:13][CH:12]=3)[CH2:7][CH2:8][CH2:9]2)=[O:39])=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6558IsobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 68929305N-(6-acetyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-(4-fluoro-phenyl)-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide

Product 1

HCID 68929051HCID 68929051, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of N-(6-acetyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-(4-fluoro-phenyl)-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide (161 mg, 0.286 mmol, 1.0 eq), isobutylamine (Aldrich, 126 mg, 1.72 mmol, 6.0 eq), NaBH(OAc)3 (Aldrich, 182 mg, 0.858 mmol, 3.0 eq) and glacial HOAc (J, T. Baker, 34 mg, 0.572 mmol, 2.0 eq) in ClCH2—CH2Cl (3 mL) was stirred at RT for 5 days. The reaction was quenched with saturated NaHCO3 (60 mL). The crude was extracted with CH2Cl2 (60 mL×3). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. Flash column chromatography (silica gel, 0-10% MeOH—CH2Cl2) afforded the title compound as a colorless thin film. MS (ESI, pos. ion) m/z: 620 (M+1).

Workup

  1. customThe reaction was quenched with saturated NaHCO3 (60 mL)
  2. extractionThe crude was extracted with CH2Cl2 (60 mL×3)
  3. washThe extract phase was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-69387cf990c9442ca892276118eff87e
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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