Benzoyl chloride → HCID 86604335, compound

HRID 1282504Notes

Reaction equation

HRID 1282504 reaction equation
[CH2:1]([NH:5][C@H:6]([C:22]([OH:24])=[O:23])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH:2]([CH3:4])[CH3:3].[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.Cl>[CH2:1]([N:5]([C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:6]([C:22]([OH:24])=[O:23])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 70076737HCID 70076737, compound

Product 1

HCID 86604335HCID 86604335, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Nα-isobutyl-Nε-benzyloxycarbonyl-L-lysine (213 mg, 0.50 mmol) in CH2Cl2 (5 mL) was added benzoyl chloride (140 mg, 1.00 mmol) and DIEA (130 mg, 1.00 mmol). The reaction mixture was stirred at room temperature for 1 h and then diluted with 1N HCl. The mixture was extracted with EtOAc, dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromatography. Elution with 70% EtOAc in hexane provided Nα-isobutyl-Nα-benzoyl-Nε-benzyloxycarbonyl-L-lysine that was further hydrogenolyzed using 10% Pd/C and then treated with 9-fluorenylmethyl chloroformate instead of N-(9-fluorenylmethoxycarbonyloxy) succinimide as outlined in step D of example 38 to provide the title compound (90% yield).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography
  5. washElution with 70% EtOAc in hexane

Sources & evidence

ORD record
ord-e598a305591b4344a58c4e3738046a13
Source dataset
uspto-grants-2002_09
Patent number
US06455587B1

Reaction notes

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