Ethanol → HCID 86657330, compound

HRID 389330Notes

Reaction equation

HRID 389330 reaction equation
[C:1]([S@@:5]([NH:7][C@H:8]([C:13]1([C:18]([O:20]CC)=O)[S:17][CH2:16][CH2:15][S:14]1)[CH2:9][CH:10]1[CH2:12][CH2:11]1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:23][NH2:24].C(O)C>>[C:1]([S@@:5]([NH:7][C@H:8]([C:13]1([C:18]([NH:24][CH3:23])=[O:20])[S:17][CH2:16][CH2:15][S:14]1)[CH2:9][CH:10]1[CH2:12][CH2:11]1)=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 86657331HCID 86657331, compound

Product 1

HCID 86657330HCID 86657330, compoundYield 93%

Procedure

A heavy-walled glass tube was charged with ethyl (S,SS)-2-[1-(tert-butylsulfinylamino)-2-cyclopropylethyl]-1,3-dithiolane-2-carboxylate (2.00 g, 5.47 mmol) and a chilled 8.0 M solution of methylamine in ethanol (5 mL, 40 mmol). The mixture was allowed to warm to room temperature and was stirred for 2 hours at which time reaction was complete by HPLC analysis. Distillation of the solvent at reduced pressure afforded the title compound (1.79 g, 93%) as an amber glass.

Workup

  1. distillationDistillation of the solvent at reduced pressure

Sources & evidence

ORD record
ord-b5f08285034d4e37a2776eea8cf196d5
Source dataset
uspto-grants-2013_02
Patent number
US08378124B2

Reaction notes

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