Hydrochloric Acid → HCID 131730259, compound

HRID 390068Notes

Reaction equation

HRID 390068 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:11]C(=O)OC(C)(C)C)([CH2:8][S:9][CH3:10])[CH2:4][O:3]1.[ClH:20]>CO>[ClH:20].[NH2:11][C:5]([CH2:8][S:9][CH3:10])([CH2:6][OH:7])[CH2:4][OH:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66953496HCID 66953496, compound

Product 1

HCID 131730259HCID 131730259, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of tert-butyl 2,2-dimethyl-5-(methylthiomethyl)-1,3-dioxan-5-ylcarbamate (2.64 g, 9.06 mmol) in methanol (10 mL) was added to a solution of concentrated hydrochloric acid (8 mL) in methanol (100 mL) and evaporated to give a yellow oil, which was purified by flash column chromatography (CH2Cl2:methanol:7 M methanolic ammonia, 5:2:1). The residue was reconverted to the hydrochloride salt by treatment with a solution of concentrated hydrochloric acid (1 mL) in methanol (5 mL) to give the 2-amino-2-(methylthiomethyl)propane-1,3-diol, hydrochloride salt (1.37 g, 100%). 1H NMR (D2O) δ 3.74 (s, 4H), 2.88 (s, 2H), 2.19 (s, 3H). 13C NMR (DMSO) δ 64.4 (2C), 57.9, 48.9, 17.5. +ESMS Found 152.0744 (M−Cl−) C5H14NO2S requires 152.0745.

Workup

  1. customevaporated
  2. customto give a yellow oil, which
  3. customwas purified by flash column chromatography (CH2Cl2:methanol:7 M methanolic ammonia, 5:2:1)

Sources & evidence

ORD record
ord-99c34ae95c764e01b6e51c7e903f7983
Source dataset
uspto-grants-2013_02
Patent number
US08383636B2

Reaction notes

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