Diisopropylethylamine → HCID 19705443, compound

HRID 727562Notes

Reaction equation

HRID 727562 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([C:12]1([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(C(C)C)CC)(C)C.[F:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][C:48]=1[F:49])[C:43](Cl)=[O:44]>C(Cl)Cl>[F:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][C:48]=1[F:49])[C:43]([NH:1][CH2:2][CH2:3][CH:4]([C:12]1([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1=[O:25])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[O:44]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27245193,4-Difluorobenzoyl chlorideHCID 19705515HCID 19705515, compound

Product 1

HCID 19705443HCID 19705443, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl α-(2-aminoethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate (549 mg, 1.36 mmol), CH2Cl2 (8.4 mL), and diisopropylethylamine (0.29 ml, 1.6 mmol) at 0° C. is added 3,4-difluorobenzoyl chloride (0.21 mL, 1.6 mmol). The solution is stirred at 0° C. for 1 hour and 16 hours at room temperature. Basic workup (CH2Cl2, NaHCO3, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc) gives 477 mg (64%) of the title compound as a white solid (mp 147°-148° C.):

Workup

  1. customBasic workup (CH2Cl2, NaHCO3, MgSO4) and purification by flash chromatography (1:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-f6eae73d9a014a019ea1d825b7ecd037
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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