Butylamine → HCID 90205447, compound

HRID 64500Notes

Reaction equation

HRID 64500 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH:17]=1)[C:12]([OH:14])=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[C:27]1[C:35]2N=NNC=2C=[CH:29][CH:28]=1.C1([N:42]=C=NC2CCCCC2)CCCCC1.C(N)CCC>C(Cl)Cl>[CH2:35]([C:15]1[C:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])=[CH:17][C:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2])=[CH:10][C:11]=1[C:12]([NH2:42])=[O:14])[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 8007ButylamineHCID 10868DicyclohexylcarbodiimideHCID 234399383,5-Bis{[tert-butyl(dimethyl)silyl]oxy}benzoic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 90205447HCID 90205447, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 mL round bottom flask equipped with a stirring bar and rubber septum was charged with 3,5-bis(tert-butyldimethylsilyloxy)benzoic acid (0.76 g, 2.0 mmol) and placed under argon. 15 mL dry DCM was added followed by the addition of hydroxybenzotriazole (HOBT; 0.3 g, 2.2 mmol) and N,N′-dicyclohexylcarbodiimide (DCC; 0.45 g, 2.2 mmol) in that order by partial removal of the septum. The resulting slurry was stirred at room temperature for 10 min. Butan-1-amine (0.3 mL, 0.22 g, 3.0 mmol) was then added drop wise and the reaction mixture was stirred overnight. The resulting heterogeneous solution was then filtered over a Buchner funnel and the filtrate was further diluted with DCM and washed with 0.5 M HCl. The aqueous layer was extracted once more with DCM and the combined organics were dried over Na2SO4. The crude reaction mixture was then concentrated on to silica gel via rotary evaporation and subjected to flash chromatography (SiO2, 10% EtOAc-hexanes; Rf=0.3 at 10% EtOAc-hexanes) to afford 13c as a white crystalline solid (0.76 g, 1.8 mmol): mp 114-117° C.; IR (neat) λmax 3294, 2929, 2857, 1632, 1583, 1543, 1438, 1334, 1253, 1163, 1027, 1004, 935, 829, 778, 692, 667, 486 cm−1; 1H NMR (400 MHz, CDCl3) δ 6.81 (d, J=2.1 Hz, 2H), 6.43 (t, J=2.1 Hz, 1H), 6.02 (app s, 1H), 3.41 (q, J=7.1 Hz, 2H), 1.58 (p, J=7.7 Hz, 2H), 1.39 (sex, J=7.2 Hz, 2H), 0.97 (s, 18H), 0.95 (t, J=7.3 Hz, 3H), 0.19 (s, 12H); 13C NMR (100 MHz, CDCl3) δ 167.3, 156.8, 137.1, 114.9, 112.1, 39.9, 31.8, 25.8, 20.3, 18.3, 13.9, −4.3; LRMS (EI) m/z=437.3 [M]+.

Workup

  1. customA 50 mL round bottom flask equipped with a stirring bar
  2. stirringthe reaction mixture was stirred overnight
  3. filtrationThe resulting heterogeneous solution was then filtered over a Buchner funnel
  4. additionthe filtrate was further diluted with DCM
  5. washwashed with 0.5 M HCl
  6. extractionThe aqueous layer was extracted once more with DCM
  7. dry with materialthe combined organics were dried over Na2SO4
  8. customThe crude reaction mixture
  9. concentrationwas then concentrated on to silica gel via rotary evaporation

Sources & evidence

ORD record
ord-b7ff0d1644c94ec886f09c3750ab8457
Source dataset
uspto-grants-2016_09
Patent number
US09447243B2

Reaction notes

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