Diisopropylethylamine → tert-Butyl 3-((2S)-benzyloxycarbonylamino-2-methoxycarbonylethyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 1167684Notes

Reaction equation

HRID 1167684 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][C@H:11]([C:32]([O:34][CH3:35])=[O:33])[CH2:12][N:13]1[C:17](=[O:18])[C:16]2([CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[NH:15][C:14]1=[O:31].[CH2:36]([O:43][C:44](ON1C(=O)CCC1=O)=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C>[CH2:36]([O:43][C:44]([NH:10][C@H:11]([C:32]([O:34][CH3:35])=[O:33])[CH2:12][N:13]1[C:17](=[O:18])[C:16]2([CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[NH:15][C:14]1=[O:31])=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 59093808tert-Butyl 3-((2S)-amino-2-methoxycarbonylethyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 86583697tert-Butyl 3-((2S)-benzyloxycarbonylamino-2-methoxycarbonylethyl)-2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.08 g (16.1 mmol) of diisopropylethylamine in 25 ml of absolute DMF are added to a solution of 3.14 g (8.48 mmol) of (34.5) and 2.11 g (8.48 mmol) of N-benzyloxycarbonyloxysuccinimide in 80 ml of absolute DMF and the mixture is left to stir at room temperature for 3 h. The solvent is removed in vacuo and the residue is chromatographed through silica gel using heptane/ethyl acetate=6/4. (34.6) is obtained after concentrating the product fractions.

Workup

  1. waitthe mixture is left
  2. customThe solvent is removed in vacuo
  3. customthe residue is chromatographed through silica gel

Sources & evidence

ORD record
ord-b5e918d3c4b84eeb8c68193ec6511333
Source dataset
uspto-grants-2003_09
Patent number
US06620820B2

Reaction notes

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