Hydrochloric Acid → HCID 69670101, compound

HRID 2038207Notes

Reaction equation

HRID 2038207 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]([CH:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH:11]1[N:17]1[C:21](=[O:22])[CH2:20][CH:19]([C:23]([OH:25])=O)[CH2:18]1)([CH3:9])[CH3:8].C(N(CC)C(C)C)(C)C.[CH2:35]([NH2:39])[CH:36]([CH3:38])[CH3:37].Cl>ClCCl.CN(C)C=O>[CH2:35]([NH:39][C:23]([CH:19]1[CH2:20][C:21](=[O:22])[N:17]([CH:11]2[CH2:12][CH:13]([CH3:16])[CH2:14][CH2:15][CH:10]2[CH:7]([CH3:8])[CH3:9])[CH2:18]1)=[O:25])[CH:36]([CH3:38])[CH3:37]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6558IsobutylamineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 69670118HCID 69670118, compound

Product 1

HCID 69670101HCID 69670101, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride ((COCl)2) (350 mg, 2.8 mmol, 240 mL) and dimethylformamide (DMF; (CH3)2NC(O)H catalytic) (20 μL) were carefully added to 1-(2-isopropyl-5-methyl-cyclohexyl)-5-oxo-pyrrolidine-3-carboxylic acid (obtained as in EXAMPLE II, 500 mg, 1.87 mmol) suspended in anhydrous dichloromethane (CH2Cl2) (10 mL). The reaction mixture slowly turned into a homogeneous solution over about 3 hours, which was then concentrated in vacuo to remove (COCl)2. The resulted raw oil was dissolved in anhydrous CH2Cl2 and subsequently added dropwise to a mixture of N,N-diisopropylethylamine (DIEA; (CH3CH2)3N) (290 mg, 2.24 mmol) and isobutylamine (H2NCH2CH(CH3)2) (160 mg, 2.24 mmol) at 0° C. with stirring. The reaction mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was poured into HCl (1 N) and extracted with CH2Cl2. The organic phases were collected, washed with brine, dried, and evaporated. Column chromatography with ethyl:acetate (50:50) provided 1-(2-isopropyl-5-methyl-cyclohexyl)-5-oxo-pyrrolidine-3-carboxylic acid isobutyl-amide (390 mg, 1.2 mmol).

Workup

  1. concentrationwhich was then concentrated in vacuo
  2. customto remove (COCl)2
  3. customThe resulted raw oil
  4. stirringstirred for 3 hours
  5. extractionextracted with CH2Cl2
  6. customThe organic phases were collected
  7. washwashed with brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-a23e3ecd18814521ade2a7ea0324e8de
Source dataset
uspto-grants-2013_11
Patent number
US08575349B2

Reaction notes

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