tert-Butyl methyl ether → HCID 68696814, 화합물

HRID 629671

반응식

HRID 629671 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[C:21]([N+:28]([O-:30])=[O:29])[CH:20]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C[N+:32](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.Cl.[C:56]([O:60][C:61](=[O:73])[C@H:62]([CH2:64][CH2:65][C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[NH2:63])([CH3:59])([CH3:58])[CH3:57].COC(C)(C)C>ClCCl.C(N(CC)CC)C>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3[CH:27]=[CH:26][C:22]([C:23]([NH:63][C@@:62]([C:61]([O:60][C:56]([CH3:58])([CH3:59])[CH3:57])=[O:73])([CH2:64][CH2:65][C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[NH2:32])=[O:24])=[C:21]([N+:28]([O-:30])=[O:29])[CH:20]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 15413tert-Butyl methyl etherHCID 208636Di-tert-butyl glutamate hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68701447HCID 68701447, 화합물

생성물 1

HCID 68696814HCID 68696814, 화합물수율 99.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

To a suspension of 17.2 g 4-(((9H-fluorene-9-yl)methoxy)carbonylamino)-2-nitrobenzoic acid in 222 ml dichloromethane were added 17.7 g of N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)-uronium-hexafluoro-phosphate. After stirring for 15 min. at room temperature a solution of 13.8 g of L-glutamic acid-di-tert.butylester hydrochloride in 172 ml dichloromethane and 12.9 ml triethylamine were added dropwise within 30 min. The mixture was stirred under nitrogen at room temperature for 20 hours. After addition of 860 ml of methyl-tert.-butylether the mixture was washed five times with aqueous sodium H carbonate (5%), 5 times with aqueous citric acid (5%) and two times with brine. The organic layer was dried over magnesium sulphate and evaporated to dryness under vacuum to give 27.9 g of crude di-tert-butyl 2-(4-(((9H-fluorene-9-yl)methoxy)carbonylamino)-2-nitrobenzamido)-L-glutamate as a yellow foam. The crude product was purified by flash chromatography using silica gel 60 and ethylacetate/n-heptane/45:55 as eluent. After evaporation of product fractions 23.8 g of di-tert-butyl-N-(4-(((9H-fluorene-9-yl)methoxy)carbonylamino)-2-nitrobenzamido)-L-glutamate were obtained as a yellow foam (HPLC, purity: 99.9% area).

후처리

  1. additionwere added dropwise within 30 min
  2. washwas washed five times with aqueous sodium H carbonate (5%), 5 times with aqueous citric acid (5%) and two times with brine
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated to dryness under vacuum

출처 및 근거

ORD 기록
ord-4170cbf80dad4d2394792b04dd667a1d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315506B2

연결된 노트

불러오는 중…