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

HRID 488898노트

반응식

HRID 488898 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.4b

후처리

  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)

출처 및 근거

ORD 기록
ord-43b5f5a56f494c5dac84abbadfed98ce
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974884B2

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