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Chloromethyl pivalate → HCID 22820629, compound

HRID 851437
Notes
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Reaction equation

HRID 851437 reaction equation
[CH3:1][C:2]([CH3:22])([O:4][C:5]([N:7]1[CH2:14][C@@H:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][C@H:8]1[C:9]([OH:11])=[O:10])=[O:6])[CH3:3].[F-].[K+].[C:25]([O:31][CH2:32]Cl)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>CN(C)C=O.O>[CH3:3][C:2]([CH3:22])([O:4][C:5]([N:7]1[CH2:14][C@@H:13]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:12][C@H:8]1[C:9]([O:11][CH2:32][O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[O:10])=[O:6])[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 87885Chloromethyl pivalateHCID 522689Potassium FluorideHCID 110121911-(1,1-Dimethylethyl) (2S,4S)-4-(phenylmethyl)-1,2-pyrrolidinedicarboxylate

Product 1

HCID 22820629HCID 22820629, compoundYield 107%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of (cis)-1-[(1,1-dimethylethoxy)carbonyl]-4-(phenylmethyl)-L-proline (3.4 g) in dry dimethylformamide (3.0 ml) is added solid potassium fluoride (1.5 g), followed by chloromethyl pivalate (2.0 g). After stirring for 16 hours at ambient temperature the mixture is diluted with water (100 ml) and extracted with ethyl acetate. The ethyl acetate solution is washed with 5% sodium bicarbonate, water, brine, and dried (MgSO4). The solvent is removed in vacuo to give an oil residue (5 g). The oil is chromatographed on silica gel (120 g) eluting with ether/hexane (1:3) to give the product (4.4 g) as an oil that solidifies on standing, melting point 60°-62° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate solution is washed with 5% sodium bicarbonate, water, brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-f7801eddbf5f4073bae75aafbd467f0b
Source dataset
uspto-grants-1983_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04384123

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes