tert-Butyl methyl ether → HCID 68696814、化合物

HRID 629671

反応式

HRID 629671 の反応式
[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

参加物

7

反応物 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、化合物

生成物 1

HCID 68696814HCID 68696814、化合物収率 99.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4170cbf80dad4d2394792b04dd667a1d
出典データセット
uspto-grants-2016_04
特許番号
US09315506B2

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