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

HRID 336453Notes

Reaction equation

HRID 336453 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-4d30e317a8cb4e37910acec7495f21fc
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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