Triethylamine → HCID 131719277, compound

HRID 2397074Notes

Reaction equation

HRID 2397074 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH:7]1[C:17]2[CH2:16][CH2:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[CH:12]([CH:22]([NH2:40])[CH2:23][O:24][CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.Br[CH2:42][C:43]([O:45][CH3:46])=[O:44].C(N(CC)CC)C>C1COCC1>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:43]([CH2:42][NH:40][CH:22]([CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:17]=2[CH2:16][CH2:15][C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]1=2)[CH2:23][O:24][CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:29]=[C:28]([C:36]([F:37])([F:38])[F:39])[CH:27]=1)([O:45][CH3:46])=[O:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 131719278HCID 131719278, compound

Product 1

HCID 131719277HCID 131719277, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the title product of Example 6, methyl bromoacetate (one equivalent) and triethylamine (one equivalent) were refluxed in THF for 22h. The reaction was partitioned between diethyl ether-water and the organic phase separated and dried (MgSO4). Solvent was removed in vacuo and the residue redissolved in ethanol. Oxalic acid was added, solvent removed in vacuo, and the residue recrystallised to give the title compound. mp 160°-165° C. (ethyl acetate-petroleum ether). 1H NMR (360MHz, DMSO-d6) 2.8-3.0 (2H, m), 3.2 (2H, s), 3.4-3.5 (6H, m), 3.6-3.65 (1H, m), 3.9-3.95 (1H, m), 4.5 (3H, s), 7.00-7.2 (8H, m), 7.9 (3H, s).

Workup

  1. customThe reaction was partitioned between diethyl ether-water
  2. customthe organic phase separated
  3. dry with materialdried (MgSO4)
  4. customSolvent was removed in vacuo
  5. dissolutionthe residue redissolved in ethanol
  6. additionOxalic acid was added
  7. customsolvent removed in vacuo
  8. customthe residue recrystallised

Sources & evidence

ORD record
ord-5b81536df5e746618c82bfa4d20109b6
Source dataset
uspto-grants-1996_02
Patent number
US05495047

Reaction notes

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