2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → HCID 90015731, compound

HRID 626904Notes

Reaction equation

HRID 626904 reaction equation
O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=[N:28][C:29]1([CH2:44][C:45]#[CH:46])[CH2:34][CH2:33][CH2:32][N:31]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:30]1=[O:43])(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[NH2:28][C:29]1([CH2:44][C:45]#[CH:46])[CH2:34][CH2:33][CH2:32][N:31]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:41])([CH3:40])[CH3:42])[C:30]1=[O:43]

Participants

4

Reactant 2

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 90015494HCID 90015494, compound

Product 1

HCID 90015731HCID 90015731, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Citric acid monohydrate (1.58 g, 7.5 mmol) was added to a solution of 3-(benzhydrylideneamino)-3-prop-2-ynyl-1-(2-trimethylsilylethoxymethyl)piperidin-2-one (which may be prepared as described in Description 23) (1.34 g, 3 mmol) in THF (30 mL) at 20° C. and the reaction was stirred for 5 days. The solution was evaporated and loaded onto an SCX cartridge (10 g) then eluted with MeOH, followed by 2M NH3 in MeOH. The fractions containing the desired product were collected and evaporated to afford 3-amino-3-prop-2-ynyl-1-(2-trimethylsilylethoxymethyl)piperidin-2-one (658 mg, 2.3296 mmol, 77.7% yield) as a yellow oil.

Workup

  1. customThe solution was evaporated
  2. washthen eluted with MeOH
  3. additionThe fractions containing the desired product
  4. customwere collected
  5. customevaporated

Sources & evidence

ORD record
ord-96dcd1a5bc504d06953bbf13e2ca76d5
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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