Diisopropylethylamine → 15-[(3,5-Bis-tert-butoxycarbonylmethoxybenzyl)-(2-carboxyethyl)carbamoyl]pentadecanoic acid 4-methoxybenzyl ester

HRID 445000Notes

Reaction equation

HRID 445000 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9](=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=O)=[CH:5][CH:4]=1.ON1C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:49]([O:53][C:54]([CH2:56][O:57][C:58]1[CH:59]=[C:60]([CH:68]=[C:69]([O:71][CH2:72][C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH:70]=1)[CH2:61][NH:62][CH2:63][CH2:64][C:65]([OH:67])=[O:66])=[O:55])([CH3:52])([CH3:51])[CH3:50]>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:27])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=[O:26])[N:62]([CH2:61][C:60]2[CH:59]=[C:58]([O:57][CH2:56][C:54]([O:53][C:49]([CH3:52])([CH3:50])[CH3:51])=[O:55])[CH:70]=[C:69]([O:71][CH2:72][C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH:68]=2)[CH2:63][CH2:64][C:65]([OH:67])=[O:66])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 58079476Hexadecanedioic acid mono-(4-methoxy-benzyl)esterHCID 59687917HCID 59687917, compound

Product 1

HCID 5807945315-[(3,5-Bis-tert-butoxycarbonylmethoxybenzyl)-(2-carboxyethyl)carbamoyl]pentadecanoic acid 4-methoxybenzyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Hexadecanedioic acid mono-(4-methoxy-benzyl) ester (0.4 g, 0.98 mmol) was dissolved in ethyl acetate (10 mL). N-Ethyl-N-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.187 g, 0.98 mmol) and 1-hydroxy-7-azabenzotriazole (0.134 g, 0.98 mmol) was added and the mixture was stirred at 50° C. for 1 hour. After cooling to room temperature, diisopropylethylamin (0.50 mL, 2.95 mmol) was added followed by 3-(3,5-Bis-tert-butoxycarbonylmethoxybenzylamino)propionic acid (0.432 g, 0.98 mmol). The mixture was stirred overnight under nitrogen at room temperature. The mixture was separated between ethyl acetate (200 mL) and water (2×100 mL). The organic phase was dried (Na2SO4), solvent removed in vacuo. The crude product was purified by RP-HPLC on C18-column, buffer A: 0.1% TFA, buffer B: MeCN+0.1% TFA; gradient 80-100% B to yield the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringThe mixture was stirred overnight under nitrogen at room temperature
  3. customThe mixture was separated between ethyl acetate (200 mL) and water (2×100 mL)
  4. dry with materialThe organic phase was dried (Na2SO4), solvent
  5. customremoved in vacuo
  6. customThe crude product was purified by RP-HPLC on C18-column, buffer A: 0.1% TFA, buffer B

Sources & evidence

ORD record
ord-3d1b42c0de77425094e9ad1fa8907dca
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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