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Triethylamine → tert-butyl N-({[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)glycinate

HRID 1715300
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HRID 1715300 반응식
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](NCC3CCCO3)=O)[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])C.[C:25]([O:29][C:30](=[O:33])[CH2:31][NH2:32])([CH3:28])([CH3:27])[CH3:26].[CH2:34]([N:36](CC)CC)C>CN(C=O)C>[C:34]([CH2:16][C:13]1[S:14][CH:15]=[C:11]([C:7]2[S:6][C:5]([NH:4][C:1]([NH:32][CH2:31][C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:33])=[O:3])=[N:9][C:8]=2[CH3:10])[N:12]=1)#[N:36]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 151417Glycine tert-butyl esterHCID 119895252'-(Acetylamino)-4'-methyl-N-(tetrahydrofuran-2-ylmethyl)-4,5'-bi-1,3-thiazole-2-carboxamide2회

생성물 1

HCID 11988393tert-butyl N-({[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)glycinate수율 124.8%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

실험 절차

N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide (Intermediate 6) (160 mg; 0.48 mmol; 1 eq) is dissolved in DMF (8 ml). A solution of glycine tert-butyl ester (63.5 mg; 0.48 mmol; 1 eq) in DMF (1 ml) and triethylamine (74 μl; 0.53 mmol; 1.10 eq) are added. After less than 1 min the mixture becomes homogeneous. After 45 min, the reaction is complete. DMF is removed under reduced pressure to afford 235.8 mg of a dark brown solid, which is purified by preparative HPLC. The purified fractions are neutralized with NaHCO3 sat. solution and the desired product is extracted with DCM. The combined organic layers are dried over MgSO4, filtered and concentrated, affording Compound (65) as a brown solid (27.30 mg; 14%).

후처리

  1. waitAfter less than 1 min the mixture becomes homogeneous
  2. customDMF is removed under reduced pressure

출처 및 근거

ORD 기록
ord-c03f8be9269448b9b861f28e062079cf
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07799814B2

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