Benzyl succinimido carbonate → HCID 58670138, compound

HRID 2249503Notes

Reaction equation

HRID 2249503 reaction equation
[NH2:1][CH:2]([CH2:8][C:9]1[C:14]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:13][CH:12]=[C:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:29]([O:36][C:37](ON1C(=O)CCC1=O)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC#N>[CH2:29]([O:36][C:37]([NH:1][CH:2]([CH2:8][C:9]1[C:14]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:13][CH:12]=[C:11]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 58670131HCID 58670131, compound

Product 1

HCID 58670138HCID 58670138, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1K (1.14 g, 2.96 mmol) in CH3CN (15 mL) was added N-(benzyloxy carbonyloxy)succinimide (819 mg, 3.25 mmol). The reaction was stirred at RT for 16 h. After this time, no starting material was detected by LC-MS. The reaction was concentrated under reduced pressure. The resulting residue was purified by silica gel (110 g) column chromatography eluting with a gradient of EtOAc (0-50%) in hexane to give the title compound as an white foam (1.50 g, 97%). LC/MS (method A): retention time=3.63 min, (M+H)+=526.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel (110 g) column chromatography
  3. washeluting with a gradient of EtOAc (0-50%) in hexane

Sources & evidence

ORD record
ord-e6a816677fb74c7b82c3f2b7cd96afb9
Source dataset
uspto-grants-2008_01
Patent number
US07314882B2

Reaction notes

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