Ammonia → (11-Carbamoylundecyl)carbamic acid tert-butyl ester

HRID 2420750Notes

Reaction equation

HRID 2420750 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)([N:25]1C=CN=C1)=O.N>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:22])[NH2:25])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 4428132Boc-12-Ado-OH

Product 1

HCID 21103219(11-Carbamoylundecyl)carbamic acid tert-butyl esterYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 12-tert-butoxycarbonylaminododecanoic acid (3) (202 mg, 0.64 mmol) and 1,1′-Carbonyldiimidazole (114 mg, 0.70 mmol) in anhydrous THF (6 mL) was stirred at room temperature for 1 hour. Methanolic ammonia (7 M, 3 mL, 21 mmol) was then added via syringe and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed by rotary evaporation and the resulting residue was subjected to Biotage silica gel column chromatography, eluting with 5% to 36% ethyl acetate in hexanes followed by 50% ethyl acetate in dichloromethane, to give the desired amide 7 (90.0 mg, 45%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.25 (m, 14H), 1.46 (s, 9H), 1.63 (m, 4H), 2.22 (t, 2H), 3.10 (m, 2H), 4.50 (br, 1H), 5.40 (br, 2H). m/z (ESI) 337 [C17H34N2O3+Na]+.

Workup

  1. stirringthe reaction mixture stirred at room temperature for 16 hours
  2. customThe solvent was removed by rotary evaporation
  3. washeluting with 5% to 36% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-56cea8c8f7b542d2911acc8cdf50fe15
Source dataset
uspto-grants-2011_06
Patent number
US07956059B2

Reaction notes

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