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Dicyclohexylcarbodiimide → S-[(Diphenylphosphino)methyl] 2-(acetylamino)ethanethioate

HRID 2250865
Notes
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Reaction equation

HRID 2250865 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:34]1([P:40]([CH2:47][SH:48])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.C(OCC)(=O)C>[C:34]1([P:40]([CH2:47][S:48][C:6](=[O:8])[CH2:5][NH:4][C:1](=[O:3])[CH3:2])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 10972AcetylglycineHCID 757711-HydroxybenzotriazoleHCID 11230015(DIPHENYLPHOSPHINO)METHANETHIOL

Product 1

HCID 11359470S-[(Diphenylphosphino)methyl] 2-(acetylamino)ethanethioateYield 96%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

N-Acetylglycine (1.90 g, 16.2 mmol) was dissolved in anhydrous DMF (75 mL). HOBt (2.48 g, 16.2 mmol) was added to the resulting solution followed by DCC (3.34 g, 16.2 mmol). Once precipitate (DCU) was observed, phosphinothiol 1b was added (3.77 g, 16.2 mmol). The reaction mixture was allowed to stir under Ar(g) for 3 h. The precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure to give a white solid. This solid was dissolved in ethyl acetate and purified by flash chromatography (silica gel, ethyl acetate). Compound 51 was isolated in 96% yield. Spectral Data. As reported previously

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a white solid
  4. custompurified by flash chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-42aa478653ac4df88c90630c1810d901
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07317129B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes