Benzyl carbazate → N'-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazinecarboxylic acid benzyl ester

HRID 1924820노트

반응식

HRID 1924820 반응식
[CH3:1][C:2]1([CH3:15])[C@@H:4]2[CH2:5][C:6]3[C:10]([C@H:3]12)=[C:9]([CH3:11])[S:8][C:7]=3[C:12]([OH:14])=O.[CH2:16]([O:23][C:24]([NH:26][NH2:27])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl.CCOCC>[CH2:16]([O:23][C:24]([NH:26][NH:27][C:12]([C:7]1[S:8][C:9]([CH3:11])=[C:10]2[C:6]=1[CH2:5][CH:4]1[C:2]([CH3:1])([CH3:15])[CH:3]12)=[O:14])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 79242Benzyl carbazateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57892448(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid

생성물 1

HCID 67520612N'-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazinecarboxylic acid benzyl ester

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid (2.2 g, 9.9 mmol), hydrazinecarboxylic acid benzyl ester (3.38 g, 20.4 mmol) and DIPEA (2 mL) in DCM (50 mL) is added TBTU (3.2 g, 10 mmol). The mixture is stirred at rt for 20 h. The mixture is diluted with Et2O (200 mL) and extracted with 1 M aq. NaOH (3×50 mL) and 1 M aq. HCl (2×50 mL). The organic phase is dried (Na2SO4), filtered and evaporated to give crude N′-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carbonyl)-hydrazinecarboxylic acid benzyl ester; LC-MS: tR=1.01 min, [M+1]+=371.25.

후처리

  1. extractionextracted with 1 M aq. NaOH (3×50 mL) and 1 M aq. HCl (2×50 mL)
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

출처 및 근거

ORD 기록
ord-69ca278e8e744d1fac265a616c687c9e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178562B2

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