Triethylamine → HCID 19850166, compound

HRID 542538Notes

Reaction equation

HRID 542538 reaction equation
[O:1]=[C:2]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].Cl.[NH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:34][CH3:35])=[C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:28]=1.C(N(CC)CC)C>ClCCl>[CH3:33][S:30]([NH:29][C:27]1[CH:28]=[C:23]([CH2:22][CH2:21][NH:20][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][C:2]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:1])[CH:24]=[CH:25][C:26]=1[O:34][CH3:35])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10777012HCID 10777012, compoundHCID 19850170HCID 19850170, compound

Product 1

HCID 19850166HCID 19850166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N'-carbonyldiimidazole (3.25 g, 0.02 moles) was added in portions under nitrogen to a suspension of 6-oxo-6-(2-phenylethylamino)hexanoic acid (4.98 g, 0.02 moles) in dry dichloromethane (100 ml). The mixture was stirred for 30 mins, the product from step (b) (5.6 g, 0.02 moles) and triethylamine (2.8 ml, 2.02 g, 0.02 moles) were added, and stirring continued for a further 4 hr. The precipitate was collected and the filtrate washed with dilute hydrochloric acid and aqueous sodium bicarbonate solution and evaporated. The residue and the original precipitate were combined and recrystallised from methanol giving the sub-title compound (6.6 g) as white needles mp 193°-195°.

Workup

  1. stirringstirring
  2. waitcontinued for a further 4 hr
  3. customThe precipitate was collected
  4. washthe filtrate washed with dilute hydrochloric acid and aqueous sodium bicarbonate solution
  5. customevaporated
  6. customrecrystallised from methanol giving the sub-title compound (6.6 g) as white needles mp 193°-195°

Sources & evidence

ORD record
ord-bd66b62685104ecca77218529e8f66cd
Source dataset
uspto-grants-1987_04
Patent number
US04657929

Reaction notes

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