Diisopropylethylamine → 4-{[(2-tert-Butoxycarbonylethyl)-(15-tert-butoxycarbonyl-pentadecanoyl)amino]methyl}benzoic acid 2,5-dioxopyrrolidin-1-yl ester

HRID 562517Notes

Reaction equation

HRID 562517 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][N:10]([CH2:34][C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=1)[C:11](=[O:33])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[B-](F)(F)(F)F.CN(C(O[N:66]1[C:71](=[O:72])[CH2:70][CH2:69][C:67]1=[O:68])=[N+](C)C)C>C1COCC1>[O:68]=[C:67]1[CH2:69][CH2:70][C:71](=[O:72])[N:66]1[O:40][C:39](=[O:41])[C:38]1[CH:37]=[CH:36][C:35]([CH2:34][N:10]([CH2:9][CH2:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:11](=[O:33])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 580794854-{[(2-tert-Butoxycarbonylethyl)-(15-tert-butoxycarbonyl-pentadecanoyl)amino]methyl}benzoic acid

Product 1

HCID 580794804-{[(2-tert-Butoxycarbonylethyl)-(15-tert-butoxycarbonyl-pentadecanoyl)amino]methyl}benzoic acid 2,5-dioxopyrrolidin-1-yl esterYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-{[(2-tert-Butoxycarbonylethyl)-(15-tert-butoxycarbonyl-pentadecanoyl)amino]methyl}benzoic acid (70 mg, 0.12 mmol) was dissolved in THF (5 mL). The mixture was cooled with an ice bath. Diisopropylethylamin (0.024 mL, 0.14 mmol) and O—(N-succinimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (42 mg, 0.14 mmol) was added. The mixture was stirred under nitrogen at 0° C. After 30 minutes the ice cooling was removed and the mixture was stirred for an additional 3 hours. Solvent removed in vacuo flowed by reevaporation from toluene. The crude product was dissolved in ethyl acetate (25 mL), washed with water (10 mL). The organic phase dried (Na2SO4), solvent removed in vacuo to yield the title compound (73 mg, 87%) which was used in subsequent step.

Workup

  1. temperatureThe mixture was cooled with an ice bath
  2. customAfter 30 minutes the ice cooling was removed
  3. stirringthe mixture was stirred for an additional 3 hours
  4. customSolvent removed in vacuo
  5. customflowed by reevaporation from toluene
  6. dissolutionThe crude product was dissolved in ethyl acetate (25 mL)
  7. washwashed with water (10 mL)
  8. dry with materialThe organic phase dried (Na2SO4), solvent
  9. customremoved in vacuo

Sources & evidence

ORD record
ord-6cbfecd6e2944f3fb786b02800ac56c8
Source dataset
uspto-grants-2011_11
Patent number
US08067362B2

Reaction notes

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