Benzoyl chloride → HCID 131736965, compound

HRID 58028Notes

Reaction equation

HRID 58028 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:24])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:23])[CH:17]([CH:19]([CH2:21][CH3:22])[CH3:20])[NH2:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:34](Cl)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[CH2:2]([O:9][C:10](=[O:24])[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:23])[CH:17]([CH:19]([CH2:21][CH3:22])[CH3:20])[NH:18][C:34](=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 131736963HCID 131736963, compound

Product 1

HCID 131736965HCID 131736965, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

D,L-isoleucyl-L-proline benzyl ester hydrochloride (1.2 g) was dissolved in dichloromethane (10 ml), cooled down to 0° C., and DIEA (860 mg) and benzoyl chloride (477 mg) were added dropwisely. The resulting mixture was allowed to warm up naturally to room temperature to react for 2 h, concentrated under reduced pressure to remove the solvent, and purified on a column to give a pale yellow oil (1.1 g, 79%).

Workup

  1. temperatureto warm up naturally to room temperature
  2. customto react for 2 h
  3. concentrationconcentrated under reduced pressure
  4. customto remove the solvent
  5. custompurified on a column

Sources & evidence

ORD record
ord-1af519a164f04ef780f8203e44dbee58
Source dataset
uspto-grants-2016_09
Patent number
US09434760B2

Reaction notes

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