Pyridine → HCID 54008227, compound

HRID 413617Notes

Reaction equation

HRID 413617 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[CH:10]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:26]([O:28][CH:29]([CH2:31][CH2:32][CH2:33][CH:34]([CH3:39])[CH2:35][CH:36]([CH3:38])[CH3:37])[CH3:30])=[O:27].N1C=CC=CC=1>C1COCC1.CCOCC>[CH2:1]([O:8][C:9](=[O:24])[CH:10]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[CH2:11][O:12][C:26]([O:28][CH:29]([CH3:30])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:39])[CH2:35][CH:36]([CH3:38])[CH3:37])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 562178benzyl 3-hydroxy-2-(phenylmethoxycarbonylamino)propanoateHCID 18520972HCID 18520972, compound

Product 1

HCID 54008227HCID 54008227, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 10 g 2-benzyloxycarbonylamino-3-hydroxy-propionic acid benzyl ester [C. G. Skinner, T. J. McCord, J. M. Ravel, W. Shive, J. Am. Chem. Soc., 78, 1956, 2412] and 10 g 6,8-dimethyl-non-2-yl chloroformate in 80 ml of THF was added a solution of 3.4 ml of pyridine in 40 ml THF at 0° C. The reaction mixture was stirred for 25 h at rt, diluted with ether and washed with 2N hydrochloric acid, saturated sodium bicarbonate and brine. The organic phase was dried and evaporated to dryness. The resulting oil was purified by chromatography on silica gel to yield 14.3 g of a colorless liquid.

Workup

  1. washwashed with 2N hydrochloric acid, saturated sodium bicarbonate and brine
  2. customThe organic phase was dried
  3. customevaporated to dryness
  4. customThe resulting oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-81259dc550ff4abb9594d99978cbc441
Source dataset
uspto-grants-2003_05
Patent number
US06569411B2

Reaction notes

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