L-Hydroxyproline → HCID 15671477, compound

HRID 1088269Notes

Reaction equation

HRID 1088269 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:37]=[CH:36][C:22]([CH2:23][O:24][C:25](SC2N=C(C)C=C(C)N=2)=[O:26])=[CH:21][CH:20]=1>O.CN(C)C=O>[CH3:17][O:18][C:19]1[CH:37]=[CH:36][C:22]([CH2:23][O:24][C:25]([N:5]2[CH2:6][C@H:2]([OH:1])[CH2:3][C@H:4]2[C:7]([OH:9])=[O:8])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 5810L-HydroxyprolineHCID 8471TriethylamineHCID 100623S-(4,6-Dimethylpyrimidin-2-yl) O-(p-methoxybenzyl) thiocarbonate

Product 1

HCID 15671477HCID 15671477, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

trans-4-Hydroxy-L-proline (13.1 g) and triethylamine (21 ml) were dissolved in 55 ml of water, and a solution of 33.44 g of S-p-methoxybenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine in 55 ml of dimethylformamide was added thereto. The resulting mixture was stirred at room temperature for 12 hours, diluted with water and washed with ethyl acetate. The aqueous layer was acidified with 5N hydrochloric acid (pH 2) under ice-cooling and extracted with ethyl acetate. The extract was washed successively with dilute hydrochloric acid and brine, dried over anhydrous sodium sulfate and distilled to obtain trans-1-(p-methoxybenzyloxycarbonyl)-4-hydroxy-L-proline. IR maxneat cm-1 : 1670, 1435, 1350, 1240, 1168.

Workup

  1. washwashed with ethyl acetate
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed successively with dilute hydrochloric acid and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled

Sources & evidence

ORD record
ord-4aab52ac0fa64ba5a6bcfa33dcf9c801
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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