1,4-Dioxane hydrochloride → 2,2-Dimethyl-propionic acid (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propyl ester

HRID 1045839Notes

Reaction equation

HRID 1045839 reaction equation
C(OC([NH:8][C@@H:9]([CH2:18][S:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=O)(C)(C)C.Cl.O1CCOCC1>ClCCl>[NH2:8][C@@H:9]([CH2:18][S:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 669742242,2-Dimethylpropionic acid (R)-2-t-butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl ester

Product 1

HCID 595430572,2-Dimethyl-propionic acid (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propyl esterYield 111.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethyl-propionic acid (R)-2-t-butoxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-propyl ester (81 g, 196 mmol) prepared in Step D was dissolved in dichloromethane (300 mL). 4N hydrochloric acid/1,4-dioxane solution (100 mL) was added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, the solvent was thoroughly removed under reduced pressure. The residue was recrystallized from diethylether, and dried to give the title compound (68 g, Yield 95%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was thoroughly removed under reduced pressure
  3. customThe residue was recrystallized from diethylether
  4. customdried

Sources & evidence

ORD record
ord-c0aa0e3c36024bb7b9fd001ffa034e21
Source dataset
uspto-grants-2013_10
Patent number
US08569307B2

Reaction notes

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