Water → HCID 68284117, compound

HRID 1527354Notes

Reaction equation

HRID 1527354 reaction equation
[NH2:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.[C:18](Cl)(=[O:25])[O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22].CCN(C(C)C)C(C)C.O>C(Cl)Cl>[CH3:17][O:16][C:14]([C@@H:4]1[CH2:3][C@H:2]([NH:1][C:18]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:25])[CH2:6][N:5]1[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 5200425(2S,4S)-1-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

Product 1

HCID 68284117HCID 68284117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate (4.6 g, 10.7 mmol) in CH2Cl2 (100 mL) were added 2,2,2-trichloroethyl carbonochloridate (1.73 mL, 12.88 mmol) and DIPEA (2.81 mL, 16.1 mmol). The reaction mixture was stirred at RT for 2 h then was poured into water. The desired compound was extracted with EtOAc (2×100 mL), the organic phases were joined, washed with 1N HCl then brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1). MS (UPLC): 421 [M+H]+, 419 [M−H]−; tR (HPLC conditions f): 1.11 min.

Workup

  1. extractionThe desired compound was extracted with EtOAc (2×100 mL)
  2. washwashed with 1N HCl
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 1:1)
  7. custom1.11 min.

Sources & evidence

ORD record
ord-f3081a41a9404411913ca411977b9584
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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