Triethylamine → HCID 19045638, compound

HRID 1781511Notes

Reaction equation

HRID 1781511 reaction equation
[NH2:1][C:2]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:14][CH3:15])=[C:7]([O:12][CH3:13])[CH:8]=2)[CH2:3]1.[CH2:21]([O:28][C:29]([N:31]([CH2:33][C:34](O)=[O:35])[CH3:32])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl>[CH2:21]([O:28][C:29]([N:31]([CH2:33][C:34]([NH:1][C:2]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:14][CH3:15])=[C:7]([O:12][CH3:13])[CH:8]=2)[CH2:3]1)=[O:35])[CH3:32])=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97053N-CarbobenzoxysarcosineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19045782HCID 19045782, compound

Product 1

HCID 19045638HCID 19045638, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-amino-1,2,3,4-tetrahydro-6,7-dimethoxynaphthalene-2-carboxylate (430 mg, 1.5 mmol), N-benzyloxycarbonylsarcosine (357 mg, 1.6 mmol), and 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride in dichloromethane (5 ml) was added triethylamine (160 mg, 1.6 mmol) under stirring at 0° C. After stirring for 2 hr, the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with 1N hydrochloric acid, sat. sodium bicarbonate, sat. sodium chloride, dried, and evaporated. The residue was purified with silica gel column chromatography [eluent; hexane-ethyl acetate (1:1 to 1:2)] to give the titled compound (550 mg, 74%).

Workup

  1. stirringAfter stirring for 2 hr
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with 1N hydrochloric acid, sat. sodium bicarbonate, sat. sodium chloride
  5. customdried
  6. customevaporated
  7. customThe residue was purified with silica gel column chromatography [eluent; hexane-ethyl acetate (1:1 to 1:2)]

Sources & evidence

ORD record
ord-3b6a2edc981a43d985cbda64672bb38c
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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