Dimethylformamide → HCID 19868624, compound

HRID 330487Notes

Reaction equation

HRID 330487 reaction equation
[C:1]([O:5][C:6](NCC(O)=O)=[O:7])([CH3:4])([CH3:3])C.[C:13](N1C=CN=C1)([N:15]1C=CN=C1)=O.C(OC1C=[C:43]([O:45][C:46](=[O:48])[CH3:47])[C:32]2[C:33]([CH3:42])=[C:34]3[N:39]([C:40](=[O:41])[C:31]=2C=1)[CH2:38][CH2:37][CH2:36][CH2:35]3)(=O)C.C[N:50](C)C=O>CN(C)C1C=CN=CC=1.O>[NH2:15][CH2:13][C:6]([O:5][C:1]1[CH:3]=[C:43]([O:45][C:46](=[O:48])[CH2:47][NH2:50])[C:32]2[C:33]([CH3:42])=[C:34]3[N:39]([C:40](=[O:41])[C:31]=2[CH:4]=1)[CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:7]

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 682631,1'-CarbonyldiimidazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 14791786HCID 14791786, compound

Product 1

HCID 19868624HCID 19868624, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Combine N-(tert.-butyloxycarbonyl)-glycine (8.8 g), 1,1'-carbonyldiimidazole (8.1 g), and N,N-dimethylformamide (40 ml) at 10° C., and, after 10 min., add 8,10-bis(acetyloxy)-1,2,3,4-tetrahydro-11-methyl-6H-benzo[b]quinolizin-6-one (2.45 g) in N,N-dimethylformamide (40 ml) followed by 4-dimethylaminopyridine (6.1 g). Stir the reaction mixture at 25° C. overnight. Dilute the reaction mixture with water (250 ml) and extract with ethyl acetate. Combine the organic extracts, and wash them sequentially with water, saturated sodium bicarbonate solution, water, 5% aqueous acetic acid, and with water. Concentrate the dried, filtered ethyl acetate solution to give a residue. Chromatograph the residue over silica gel, and elute the column with 1°-2% methanol in dichloromethane. Combine fractions to give 8,10bis[(aminoacetyl)oxy]-11-methyl-1,2,3,4-tetrahydro-6H-benzo[b]quinolizine-6-one, m.p. 163°-164° C. (from MeOH-CH2Cl2). Use this material directly in the next step.

Workup

  1. extractionextract with ethyl acetate
  2. washwash them sequentially with water, saturated sodium bicarbonate solution, water, 5% aqueous acetic acid
  3. concentrationConcentrate the dried
  4. filtrationfiltered ethyl acetate solution
  5. customto give a residue
  6. washChromatograph the residue over silica gel, and elute the column with 1°-2% methanol in dichloromethane

Sources & evidence

ORD record
ord-56096c859a56465cb0b3c268e6caa7a8
Source dataset
uspto-grants-1990_01
Patent number
US04897391

Reaction notes

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