4-Nitrobenzoyl chloride → (S)-cyclopentyl 4-methyl-2-(4-nitrobenzamido)pentanoate

HRID 1509967Notes

Reaction equation

HRID 1509967 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][C@H:14]([C:19]([O:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17].C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:17][CH:16]([CH3:18])[CH2:15][C@H:14]([NH:13][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:19]([O:21][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:20]

Participants

6

Reactant 4

HCID 85024-Nitrobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate

Product 1

HCID 57687133(S)-cyclopentyl 4-methyl-2-(4-nitrobenzamido)pentanoateYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Nitrobenzoyl chloride (0.60 g, 3.9 mmol) in DCM (2 ml) was added dropwise over 10 min to a solution of cyclopentyl L-leucinate (0.70 g, 3.5 mmol) and diisopropylethylamine (0.94 ml, 5.3 mmol) in DCM (10 ml) at −5° C. under an atmosphere of nitrogen. On completion of the addition, the reaction mixture was allowed to warm to RT and stirred for a further 30 min. The reaction mixture was poured on to sat. aq. NaHCO3 and the aqueous layer was extracted with DCM. The organic extracts were combined, washed with brine, dried over MgSO4 and evaporated under reduced pressure afford the title compound as an oily solid (1.2 g, 87%). m/z 347.1 [M+H]+.

Workup

  1. additionOn completion of the addition
  2. extractionthe aqueous layer was extracted with DCM
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0c3b827bcacf4641beaf14fce28c085a
Source dataset
uspto-grants-2012_07
Patent number
US08211900B2

Reaction notes

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