Acetic Acid → N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, ethyl ester

HRID 231946

反応式

HRID 231946 の反応式
N#N.[CH3:3][C:4]([CH3:29])([O:6][C:7]([NH:9][C@H:10]([C:26]([OH:28])=[O:27])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:8])[CH3:5].[N+:30](=C)=[N-:31].[C:33](O)(=O)[CH3:34].N#N.CC(C)(OC(N[C@H](C(OC)=O)CCCCNC(OCC1C=CC=CC=1)=O)=O)C>C(OCC)(=O)C.CC(C)=O.CCCCCC>[N:30]#[N:31].[CH3:5][C:4]([CH3:29])([O:6][C:7]([NH:9][C@H:10]([C:26]([O:28][CH2:33][CH3:34])=[O:27])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])=[O:8])[CH3:3]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 86742311N2 [(1,1-dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysineHCID 131714291N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, methyl ester

生成物 1

HCID 131716012N2 [(1,1-Dimethylethoxy)carbonyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, ethyl ester

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N2 -[(1,1-Dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine (5.48 g., 14.4 mmole) is dissolved in ethyl acetate (130 ml.). Diazomethane is added until a yellow color persists. Acetic acid is added to quench the excess diazomethane, and the volatiles are evaporated. The residue is partitioned between ethyl acetate and saturated sodium bicarbonate, the organic layer is dried over sodium sulfate, filtered, and then the volatiles are evaporated. Purification of the residue by column chromatography on LPS-1 silica eluting with 30% ethyl acetate/hexane yields 4.0 g. of N2 -[(1,1-dimethylethoxy)carbonyl]-N6 -[(phenylmethoxy)carbonyl]-L-lysine, methyl ester. TLC (silica gel; hexane:acetone, 1:1) Rf =0.69.

後処理

  1. customto quench the excess diazomethane
  2. customthe volatiles are evaporated
  3. customThe residue is partitioned between ethyl acetate and saturated sodium bicarbonate
  4. dry with materialthe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customthe volatiles are evaporated
  7. customPurification of the residue by column chromatography on LPS-1 silica eluting with 30% ethyl acetate/hexane
  8. customyields 4.0 g

出典と根拠

ORDレコード
ord-21245ab6dfb242aea21b6a51d4edb4cb
出典データセット
uspto-grants-1989_07
特許番号
US04849414

関連ノート

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