1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → HCID 22877900, compound

HRID 1488858Notes

Reaction equation

HRID 1488858 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C[N:28]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[N:54]1([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:61][CH2:60][CH2:59][C@H:55]1[C:56](O)=[O:57].C(=O)([O-])O.[Na+]>C(#N)C.O.C(N(CC)CC)C>[NH2:2][C:3]1[CH:4]=[C:5](/[CH:11]=[C:12](\[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)/[C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:62]([N:54]1[CH2:61][CH2:60][CH2:59][C@H:55]1[C:56]([NH2:28])=[O:57])([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63]

Participants

8

Reactant 4

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 9976854HCID 9976854, compound

Product 1

HCID 22877900HCID 22877900, compoundYield 92.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

(E)-3-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrile hydrochloride (998 mg, 2.65 mmols), 1,300 mg of a BOP reagent and 605 mg of Boc-L-Pro were dissolved in 50 ml of acetonitrile, and 0.8 ml of triethylamine were added thereto. The mixture was reacted at room temperature for 18 hours and at 50° C. for 20 hours. One-hundred milliliters of water and a small amount of sodium hydrogencarbonate were added thereto, and the resulting mixture was extracted with ethyl acetate. Subsequently, the extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The product was purified using a silica-gel column (eluent, dichloromethane), and then concentrated to produce 1,310 mg (2.44 mmols) of the final product in a yield of 92%.

Workup

  1. customThe mixture was reacted at room temperature for 18 hours and at 50° C. for 20 hours
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialSubsequently, the extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0e8b233837f34b73aa2d51c7e499b653
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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