1,2-Dichloroethane → HCID 10606626, compound

HRID 733316Notes

Reaction equation

HRID 733316 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH:20]1[CH:21]=[CH:22][C:23]2N(O)N=[N:26][C:24]=2[CH:25]=1.NC1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:15])[NH:26][C:24]1[CH:25]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 10606626HCID 10606626, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of pyrrolidine-1,2(S)-dicarboxylic acid 1-t-butyl ester (50 g, 233 mmol), EDC (45 g, 233 mmol) and HOBT (12 g, 77.5 mmol) in 1500 ml of dichloromethane was cooled to 0° C. and aniline (21 ml, 233 mmol) was added dropwise over a period of 15 minutes. The mixture was stirred over night, evaporated and partitioned between ethyl acetate and 1N-HCl. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and evaporated. The crude solid was crystallized from diethyl ether. Yield: 104 g (quantitative).

Workup

  1. customevaporated
  2. custompartitioned between ethyl acetate and 1N-HCl
  3. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe crude solid was crystallized from diethyl ether

Sources & evidence

ORD record
ord-3e7ce3cd8b344592ad9564ad10a0b0de
Source dataset
uspto-grants-2009_09
Patent number
US07589091B2

Reaction notes

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