Dodecylamine → HCID 131715429, compound

HRID 2413845Notes

Reaction equation

HRID 2413845 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH:14]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:15][C:16]([NH:18][C@H:19]([C:27](O)=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17]>C1COCC1>[C:30]([NH:14][CH2:15][C:16]([NH:18][C@H:19]([C:27]([NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:28])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:17])([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]

Participants

4

Reactant 2

HCID 13583DodecylamineHCID 6998938Z-Gly-phe-OH

Product 1

HCID 131715429HCID 131715429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dodecylamine (924 mg.) in 20 ml. THF is added dropwise to a 0° C. solution of 1.78 g. z-Gly-Phe and 1.02 g. DDC in 30 ml. THF under N2 and stirred at 0° C. for 4 hours. The reaction mixture is filtered, the filtrate evaporated in vacuo to give 3.53 g. crude product, which was chromatographed on 100 g. silica gel in CHCl3 /EtOAc (2:1) to give 890 mg. product (34%). NMR (CDCl3, δ): 7.7m (1H); 7.3 d (10 Hz); 6.6 m (1H); 6.2 (1H); 5.2 s (2H); 4.8 m (1H); 3.9 d, J=6 Hz (2H); 3.1 m (4H); 1.3 bs (20H); 0.9 m (3H).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate evaporated in vacuo
  3. customto give 3.53 g
  4. customcrude product, which was chromatographed on 100 g
  5. customsilica gel in CHCl3 /EtOAc (2:1) to give 890 mg
  6. custom7.3 d (10 Hz)

Sources & evidence

ORD record
ord-cb16f2a42c774a7a8195f10df67ff022
Source dataset
uspto-grants-1988_01
Patent number
US04719312

Reaction notes

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