1,3-DI-Boc-2-methylisothiourea → HCID 178454258, compound

HRID 2358932Notes

Reaction equation

HRID 2358932 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].[C:20]([O:24][C:25]([NH:27][C:28](=[N:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])SC)=[O:26])([CH3:23])([CH3:22])[CH3:21]>C1COCC1.CO.C1COCC1>[NH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:28]([NH:27][C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])=[N:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]

Participants

5

Reactant 2

HCID 5466031,3-DI-Boc-2-methylisothioureaHCID 10199351BIS(8-AMINOOCTYL)AMINE

Product 1

HCID 178454258HCID 178454258, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of 1,17-diamino-9-azaheptadecane 3 (4.9 g, 15.06 mmol) in THF/CH3OH 5/3 (80 mL) at 50° C., a solution of N,N′-bis(tert-butoxycarbonyl)-S-methylisothiourea (1.456 g, 5.02 mmol) in THF (25 mL) was added dropwise over 1 h. After 16 h, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (6% methanol, 4% triethylamine, 90% ethyl acetate), affording 12 as a pale yellow oil, 3.51 g (70%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (6% methanol, 4% triethylamine, 90% ethyl acetate)

Sources & evidence

ORD record
ord-50f7af91c1e24a149147b554c3192051
Source dataset
uspto-grants-2014_04
Patent number
US08685953B2

Reaction notes

Loading…