p-Toluenesulfonic acid → (C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2Ph

HRID 1246734Notes

Reaction equation

HRID 1246734 reaction equation
[N:1]([C:38]([CH2:40][O:41][CH2:42][C:43]([OH:45])=O)=[O:39])([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(Cl)Cl.[NH2:49][CH2:50][C:51]([NH:53][CH2:54][C:55]([NH:57][CH2:58][C:59]([O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:60])=[O:56])=[O:52].CC1C=CC(S(O)(=O)=O)=CC=1>CCN(CC)CC>[N:1]([C:38]([CH2:40][O:41][CH2:42][C:43]([NH:49][CH2:50][C:51]([NH:53][CH2:54][C:55]([NH:57][CH2:58][C:59]([O:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:60])=[O:56])=[O:52])=[O:45])=[O:39])([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6344DichloromethaneHCID 15431793Gly-Gly-Gly-OCH2PhHCID 18689621[2-(Dioctadecylamino)-2-oxoethoxy]acetic acid

Product 1

HCID 101159097(C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2PhYield 89%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of (C18H37)2NCOCH2OCH2COOH (1.0 g, 1.5 mmol) in CH2Cl2 (30 mL) 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (0.31 g, 1.6 mmol) was added and the reaction was stirred at room temperature. After 0.5 h Gly-Gly-Gly-OCH2Ph.TsOH (0.66 g, 1.5 mmol) and Et3N (0.6 mL) were added and the mixture was stirred overnight. The reaction mixture was then washed with water (20 mL), 0.5 N HCl (20 mL), water (20 mL), 10% aqueous Na2CO3 (20 mL), brine (20 mL), and then dried over MgSO4. The solvent was evaporated and the residue was crystallized form MeOH to yield (C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2Ph as a deliquescent white solid (1.26 g, 89%), mp 41–42° C. 1H-NMR (300 MHz, δ, CDCl3) 0.86 (6H, t, J=6.9 Hz), 1.24 (64H, m), 1.49 (4H, bs), 3.04 (2H, t, J=7.5 Hz), 3.24 (2H, t, J=7.5 Hz), 3.95–4.05 (6H, m), 4.09 (2H, s), 4.29 (2H, s), 5.12 (2H, s), 7.23 (1H, t, J=6.0 Hz), 7.30–7.35 (5H, m), 7.93 (1H, t, J=5.7 Hz), 8.27 (1H, t, J=5.7 Hz). 13C-NMR (75 MHz, δ, CDCl3): 13.9, 22.5, 26.7, 26.9, 27.4, 28.6, 29.2, 29.3, 29.6, 31.8, 41.0, 42.9, 46.3, 46.7, 66.9, 69.6, 71.7, 128.2, 128.4, 128.6, 135.3, 168.6, 169.7, 169.8, 170.0, 171.5. IR (KBr, cm−1): 1749 (CO), 1651 (CO).

Workup

  1. stirringthe mixture was stirred overnight
  2. washThe reaction mixture was then washed with water (20 mL), 0.5 N HCl (20 mL), water (20 mL), 10% aqueous Na2CO3 (20 mL), brine (20 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated
  5. customthe residue was crystallized form MeOH

Sources & evidence

ORD record
ord-1fb348c203724f70aaa20cc49de1dc24
Source dataset
uspto-grants-2006_10
Patent number
US07129208B2

Reaction notes

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