Chlorosuccinimide → HCID 69810193, compound

HRID 2190050Notes

Reaction equation

HRID 2190050 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-fab86b5e7bc04933af600f6d0089642f
Source dataset
uspto-grants-2012_12
Patent number
US08324221B2

Reaction notes

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