tert-Butyl (3-aminopropyl)carbamate → HCID 21022371, compound

HRID 1794606Notes

Reaction equation

HRID 1794606 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][S:17][C:11]=2[N:10]=[C:9]1[CH:19](Br)[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([NH:30][CH2:31][CH2:32][CH2:33][NH2:34])([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CCO>[C:26]([O:25][C:23](=[O:24])[NH:30][CH2:31][CH2:32][CH2:33][NH:34][CH:19]([C:9]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][S:17][C:11]=2[N:10]=1)[CH2:20][CH3:21])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 22222345HCID 22222345, compound

Product 1

HCID 21022371HCID 21022371, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A reaction mixture of 32 and N-Boc-1,3-diaminopropane (800 μl) in EtOH (10 ml) was heated at 90° C. for 14 h, then cooled to room temperature and purified by preparative HPLC to give 33 (350 mg) at the yield of 52% for two steps. 33 had an analytical HPLC retention time=3.03 min. (Column: YMC S5 Combiscreen 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O, 0.2% H3PO4) 1H-NMR (400 MHz, CDCl3): δ 7.25–7.41 (m, 5H), 5.80 (d, J=16.41 Hz, 1H), 5.16 (d, J=16.41 Hz, 1H), 5.04 (brs, 1H), 4.66 (t, J=5.82 Hz, 1H), 3.11 (m, 2H), 2.89 (s, 3H), 2.72 (m, 1H), 2.57 (m, 1H), 2.02 (m, 2H), 2.74 (m, 2H), 1.43 (s, 9H), 0.84 (t, J=7.36 Hz, 3H).

Workup

  1. temperaturecooled to room temperature
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-47f0ee8f23a64d49bf6c97098d4f9230
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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