Water → Tri-Boc Lysine-beta-aminoethyl Ester

HRID 1040295Notes

Reaction equation

HRID 1040295 reaction equation
[C:1]([N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:25](C(CN)O)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].[CH3:36][CH2:37][N:38]=C=NCCCN(C)C.Cl.O>ClCCl.CN(C)C1C=CN=CC=1>[NH2:38][CH2:37][CH2:36][O:16][C:15](=[O:17])[C@:9]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])([CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])[N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22707757Propanoic acid, 3-amino-2-hydroxy-, 1,1-dimethylethyl esterHCID 22792075Di-tert-butoxycarbonyl-lysine

Product 1

HCID 131730895Tri-Boc Lysine-beta-aminoethyl EsterYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Di-Boc lysine (770 grams, 2.2 mol) was dissolved in dichloromethane (4 liters). Bocethanolamine (340 grams, 2.1 mol) was added to the solution, along with 4-dimethylaminopyridine (50 grams.) EDC-HCl (450 grams, 2.35 mol) was added and the mixture was allowed to stir overnight at room temperature. Water (2 liters) was added and the mixture was stirred for 30 minutes. The layers were separated, and the aqueous layer was extracted with dichloromethane. The combined organics were washed with saturated sodium bicarbonate, 1N HCl solution, and brine. Solvent was removed under reduced pressure to give an oil. Mass recovery was 770 grams (68% yield).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organics were washed with saturated sodium bicarbonate, 1N HCl solution, and brine
  6. customSolvent was removed under reduced pressure
  7. customto give an oil

Sources & evidence

ORD record
ord-02a25817089144c5a5880e63fe2b155b
Source dataset
uspto-grants-2013_10
Patent number
US08552217B2

Reaction notes

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