Hydrogen Sulfide → 2-Amino-2-benzyloxymethyl-1-phthalimido-ethane

HRID 1733781

Reaction equation

HRID 1733781 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([N:23]=[N+]=[N-])[CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.O.S>C(O)(=O)C>[NH2:23][CH:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:11][N:12]1[C:13](=[O:22])[C:14]2=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]2[C:16]1=[O:17]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 194385322-Benzyloxymethyl-2-azido-1-phthalimido-ethaneHCID 66926435Pyridine water

Product 1

HCID 194385522-Amino-2-benzyloxymethyl-1-phthalimido-ethaneYield 20%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Into a stirred solution of 2-benzyloxymethyl-2-azido-1-phthalimido-ethane (500 mg, 1.5 mmol) in 4:1 pyridine/water (25 ml) was bubbled hydrogen sulphide, and the reaction was monitored by TLC. After 4 hours, the gas flow was stopped, and the reaction flask sealed. The intense green reaction mixture was stirred for another 17 hours. TLC indicated full conversion of the starting material. Glacial acetic acid was added to pH 7, and the reaction mixture was evaporated to dryness in vacuo. After evaporation from ethanol (3×25 ml), the resulting brown solid was purified by chromatography. Yield=20%. The structure was confirmed by NMR and IR.

Workup

  1. customthe reaction flask sealed
  2. customthe reaction mixture was evaporated to dryness in vacuo
  3. customAfter evaporation from ethanol (3×25 ml)
  4. customthe resulting brown solid was purified by chromatography

Sources & evidence

ORD record
ord-9bdd63524dd145a28169bfc350ac3342
Source dataset
uspto-grants-1996_07
Patent number
US05531978

Linked notes

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