Acetic Anhydride → HCID 178471579, compound

HRID 2350905Notes

Reaction equation

HRID 2350905 reaction equation
[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:43])[C:11]2[CH:17]=[C:16]([CH2:18][NH:19][CH2:20][C:21]3[CH:42]=[CH:41][C:24]([C:25]([NH:27][C@H:28]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:26])=[CH:23][CH:22]=3)[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:44](OC(=O)C)(=[O:46])C>C(O)=O>[C:1]([NH:7][C:8]1[N:9]=[C:10]([OH:43])[C:11]2[CH:17]=[C:16]([CH2:18][N:19]([CH2:20][C:21]3[CH:42]=[CH:41][C:24]([C:25]([NH:27][C@H:28]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:26])=[CH:23][CH:22]=3)[CH:44]=[O:46])[CH:15]=[N:14][C:12]=2[N:13]=1)(=[O:6])[C:2]([CH3:3])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178471576HCID 178471576, compound

Product 1

HCID 178471579HCID 178471579, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1.0 g. (1.7 mmol) of diethyl N-[N-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-ylmethyl)-4-aminomethylbenzoyl]-glutamate in 10 mL of 98% formic acid was added 0.35 g. (0.33 mL, 3.5 mmol) of acetic anhydride. The mixture was stirred at 25° C. for 1 h. The solvent was removed under reduced pressure and the solid dissolved in methylene chloride and extracted twice with a saturated solution of sodium bicarbonate. The aqueous layers were back extracted with methylene chloride, and the organic layers combined and dried over anhydrous magnesium sulfate. The solvent was evaporated to dryness to give a quantitative yield of diethyl N-[N-(2-pivaloylamino-4-hydroxypyrido[2,3-d]pyrimidin-6-ylmethyl)-N-formyl-4-aminomethylbenzoyl]-glutamate which can be employed for further processing without further purification; 1H NMR (Me2SO d6) delta 1.11-1.18 (m, 6H), 1.24 (s, 9H), 1.9-2.15 (m, 2H), 2.39-2.44 (m, 2H), 4.39-4.42 (m, 3H), 4.53-4.55 (m, 2H), 7.21-7.44 and 7.34-7.37 (m, 2H, AA'BB'), 7.76-7.78 and 7.81-7.84 (m, 2H, AA'BB'), 8.12 and 8.13 (s, 1H), 8.61-8.78 (m, 2H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe solid dissolved in methylene chloride
  3. extractionextracted twice with a saturated solution of sodium bicarbonate
  4. extractionThe aqueous layers were back extracted with methylene chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-402be7e4c99545b3a2f434f177fa5575
Source dataset
uspto-grants-1989_10
Patent number
US04871746

Reaction notes

Loading…