Acetic Acid → HCID 67842363, compound

HRID 1492824Notes

Reaction equation

HRID 1492824 reaction equation
[Na].[O-]CC.[Na+].[C:6]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH2:17]([O:19][C:20](=[O:43])/[CH:21]=[CH:22]/[C@@H:23]1[CH2:27][C@@H:26]([O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:25][N:24]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH3:18].C(O)(=O)C>C(O)C>[C:39]([O:38][C:36]([N:24]1[CH2:25][C@H:26]([O:28][Si:29]([C:32]([CH3:33])([CH3:34])[CH3:35])([CH3:30])[CH3:31])[CH2:27][C@H:23]1[CH:22]([CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:43])[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([O:14][CH2:15][CH3:16])=[O:13])=[O:37])([CH3:42])([CH3:40])[CH3:41]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 10692325HCID 10692325, compound

Product 1

HCID 67842363HCID 67842363, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To sodium metal (6.90 g, 0.30 mol), absolute ethanol (300 ml) was gradually added to prepare sodium ethoxide, and a solution of diethyl malonate (151.9 ml, 1.0 mol) in ethanol (500 ml) was dropwise added thereto at room temperature. A solution of (E)-3-[(2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxypyrrolidin-2-yl]-acrylic acid ethyl ester (400 g, 1.0 mol, compound of Reference Example 1-4) in ethanol (1500 ml) was further added thereto at the same temperature, and stirred overnight. After acetic acid (17.2 ml, 0.30 mol) was added thereto under cooling with ice, the reaction solution was concentrated under reduced pressure to obtain triethyl 2-[(2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxypyrrolidin-2-yl]-1,1,3-propanetricarboxylate (558.3 g) as a crude oil.

Workup

  1. customat room temperature
  2. temperatureunder cooling with ice
  3. concentrationthe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a26c5f94e0a4355b9ec9305bb2b3fd7
Source dataset
uspto-grants-1994_12
Patent number
US05374720

Reaction notes

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