tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamate → HCID 57880411, compound

HRID 643549Notes

Reaction equation

HRID 643549 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[C:9]([OH:23])[CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)C(=O)O1.[C:26]([O:30][C:31]([O:33][NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:32])([CH3:29])([CH3:28])[CH3:27]>C1(C)C=CC=CC=1>[C:37]([O:36][C:35]([N:34]([O:33][C:31]([O:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:32])[C:6](=[O:8])[CH2:5][C:9]([CH:10]1[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:14][CH2:15]1)=[O:23])=[O:41])([CH3:40])([CH3:39])[CH3:38]

Participants

4

Reactant 2

HCID 2728863tert-Butyl (((1,1-dimethylethoxy)carbonyl)oxy)carbamateHCID 57880560HCID 57880560, compound

Product 1

HCID 57880411HCID 57880411, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl 4-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)(hydroxy)methyl]piperidine-1-carboxylate (8.99 g, 25.3 mmol) and t-butyl N-(t-butoxycarbonyloxy)carbamate (5.90 g, 25.3 mmol) in toluene (200 mL) was stirred at 65° C. for 14 h, then at rt for 36 h. The reaction mixture was concentrated and the residue was purified by flash chromatography (silica, 25% ethyl acetate/hexanes) to afford tert-butyl 4-(3-{(tert-butoxycarbonyl)[(tert-butoxycarbonyl)oxy]amino}-3-oxopropanoyl)piperidine-1-carboxylate. H NMR analysis was consistent with product but complex due to carbamate rotamers.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography (silica, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-347df700bd0240a1834ef15b1f758935
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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