Chlorosuccinimide → HCID 69810193, compound

HRID 529112Notes

Reaction equation

HRID 529112 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]2[N:16]([C:31]3[C:32]4[C@H:39]([CH3:40])[CH2:38][C@@H:37]([O:41][C:42](=[O:52])[C:43]5[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][CH:44]=5)[C:33]=4[N:34]=[CH:35][N:36]=3)[CH2:17][C:18]3([CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[C:11]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:53]N1C(=O)CCC1=O>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:15]([Cl:53])=[CH:14][CH:13]=[C:12]2[N:16]([C:31]3[C:32]4[C@H:39]([CH3:40])[CH2:38][C@@H:37]([O:41][C:42](=[O:52])[C:43]5[CH:44]=[CH:45][C:46]([N+:49]([O-:51])=[O:50])=[CH:47][CH:48]=5)[C:33]=4[N:34]=[CH:35][N:36]=3)[CH2:17][C:18]3([CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:22][CH2:23]3)[C:11]=12)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 69811874HCID 69811874, compound

Product 1

HCID 69810193HCID 69810193, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl 4-((tert-butoxycarbonylamino)methyl)-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (17 mg, 0.024 mmol) in DCM (0.5 mL) was added 1-chloropyrrolidine-2,5-dione (NCS) (5.7 mg, 0.043 mmol). The reaction mixture was stirred at about room temperature for 48 hours. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by column chromatography (hexanes:EtOAc, 1:1) to give tert-butyl 4-((tert-butoxycarbonylamino)methyl)-5-chloro-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (5 mg, 28%). LCMS (APCI+) m/z 749, 751 [M+H]+; Rt=4.66 min.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (hexanes:EtOAc, 1:1)

Sources & evidence

ORD record
ord-3373e9f20f0543df88a7f31e33aed14a
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

Loading…