1-(1,1-Dimethylethyl) 3-ethyl (3R,4R)-4-[[(4-chlorophenyl)amino]carbonyl]-1,3-pyrrolidinedicarboxylate → HCID 86600790, compound

HRID 1987180Notes

Reaction equation

[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11](=[O:20])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1)=[O:5])[CH3:2]>Cl.C(O)(C)C>[ClH:19].[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11](=[O:20])[NH:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

Compound 39b (1.6 g; 4.03 mmol) is dissolved in 6N HCl in isopropanol (12.5 ml) and the reaction mixture is stirred for 2 h at 25° C. The reaction mixture is evaporated to dryness and the crude product is crystallized twice from diethylether to yield an off-white solid. Yield: 1.44 g (107.2%), ESI-MS: m/z=297 [M+H]+, Cl-Pattern

Workup

customThe reaction mixture is evaporated to dryness
customthe crude product is crystallized twice from diethylether
customto yield an off-white solid

Sources & evidence

ORD record: ord-984569ba77cf42f8a1e2b704fa18bf68
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550487B2

Reaction notes

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