1,2-Dichloroethane → HCID 10606626, compound

HRID 2186474Notes

Reaction equation

HRID 2186474 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.CCOC(C)=O>[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

7

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 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-Boc-L-proline (1.0 g, 4.65 mmol), aniline (0.433 g. 4.65 mmol), and HOBT (0.753 g, 5.58 mmol) in 10 mL of CH2Cl2 was added EDC (1.07 g, 5.58 mmol) and the solution was stirred overnight. To the solution was added 70 mL of EtOAc and washed with 50 mL 3N HCl, 50 mL water, 50 mL NaHCO3 (sat.), 50 mL 10% K2CO3, and 50 mL brine. The organic layer was then dried over MgSO4, filtered and concentrated under reduced pressure to give a white solid (1.2 g. 89%. ES (+) MS m/e=291 (M+H).

Workup

  1. washwashed with 50 mL 3N HCl, 50 mL water, 50 mL NaHCO3 (sat.), 50 mL 10% K2CO3, and 50 mL brine
  2. dry with materialThe organic layer was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a white solid (1.2 g. 89%. ES (+)

Sources & evidence

ORD record
ord-21175929c880421db951b670a2d4eb69
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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