Diisopropylethylamine → HCID 67452542, compound

HRID 591138Notes

Reaction equation

HRID 591138 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH2:8][C:9]([CH3:14])([CH3:13])[CH2:10][NH:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[C:25]([O:35]N1C(=O)CCC1=O)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=O>C(Cl)(Cl)Cl>[CH2:28]([O:27][C:25](=[O:35])[N:11]([CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])[CH3:12])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 721119741345532-72-0

Product 1

HCID 67452542HCID 67452542, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of (2,2-Dimethyl-3-methylamino-propyl)-carbamic acid tert-butyl ester (compound PP) (1.05 g, 4.85 mmol) in CHCl3 (10 mL) at ambient temperature was added DIEA (0.84 mL, 4.85 mmol) followed by Cbz-OSu (1.21 g. 4.85 mmol), and the reaction mixture was stirred for 2 h. The reaction mixture then was diluted with CHCl3 (100 mL), and washed with water (2×50 mL) and brine (50 mL). The organic layer was separated and dried over Na2SO4. The removal of the solvents in vacuo yielded crude compound QQ in quantitative yield (1.78 g, 4.85 mmol) as a foamy solid. LC-MS [M+H] 351.6 (C19H30N2O4+H, calc: 351.2). Compound QQ was used directly in the next reaction without further purification.

Workup

  1. washwashed with water (2×50 mL) and brine (50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customThe removal of the solvents in vacuo
  5. customyielded crude compound QQ in quantitative yield (1.78 g, 4.85 mmol) as a foamy solid
  6. customCompound QQ was used directly in the next reaction without further purification

Sources & evidence

ORD record
ord-d0f9696fe8ad4291b62ff0a84936d843
Source dataset
uspto-grants-2016_01
Patent number
US09238020B2

Reaction notes

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