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

HRID 1515244Notes

Reaction equation

HRID 1515244 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-7ddd82d662ec4bf4a9b5a38ee12e5ead
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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