Diisopropylethylamine → (S)-2-{4-[(15-tert-Butoxycarbonyl-pentadecanoylamino)-methyl]-benzoylamino}-pentanedioic acid 1-tert-butyl ester

HRID 562544ノート

反応式

HRID 562544 の反応式
[C:1]([O:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH:24][CH2:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][CH:27]=1)=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(ON1C(=O)CCC1=O)=[N+](C)C)C.[NH2:64][C@H:65]([C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])[CH2:66][CH2:67][C:68](=[O:70])[OH:69]>C1COCC1.CN1C(=O)CCC1>[C:74]([O:73][C:71](=[O:72])[C@@H:65]([NH:64][C:30](=[O:32])[C:29]1[CH:28]=[CH:27][C:26]([CH2:25][NH:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:34][CH:33]=1)[CH2:66][CH2:67][C:68]([OH:70])=[O:69])([CH3:77])([CH3:75])[CH3:76]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamateHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 596879104-[(15-Tert-butoxycarbonylpentadecanoylamino)methyl]benzoic acid

生成物 1

HCID 58079446(S)-2-{4-[(15-tert-Butoxycarbonyl-pentadecanoylamino)-methyl]-benzoylamino}-pentanedioic acid 1-tert-butyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

4-[(15-tert-butoxycarbonylpentadecanoylamino)methyl]benzoic acid (413 mg, 0.868 mmol) was dissolved in THF (5 mL), the solution was cooled with an icebath. DIPEA (0.33 mL, 1.91 mmol) and TSTU (314 mg, 1.04 mmol) were added. The mixture was stirred under nitrogen while cooling was maintained. After 30 minutes the icebath was removed and the mixture was stirred for additional 3 hours at room temperature. The mixture was diluted with NMP (5 mL) and H-GluOtBu (0.21 g, 1.04 mmol) was added, the mixture was stirred overnight at room temperature. The mixture was separated between ethyl acetate (100 mL) and water (100 mL), the organic phase dried (Na2SO4) and solvent removed in vacuo. The crude material was purified on silica using DCM/ethanol (90:10) to give (S)-2-{4-[(15-tert-Butoxycarbonyl-pentadecanoylamino)-methyl]-benzoylamino}-pentanedioic acid 1-tert-butyl ester.

後処理

  1. temperaturethe solution was cooled with an icebath
  2. temperaturewhile cooling
  3. temperaturewas maintained
  4. customAfter 30 minutes the icebath was removed
  5. stirringthe mixture was stirred for additional 3 hours at room temperature
  6. additionwas added
  7. stirringthe mixture was stirred overnight at room temperature
  8. customThe mixture was separated between ethyl acetate (100 mL) and water (100 mL)
  9. dry with materialthe organic phase dried (Na2SO4) and solvent
  10. customremoved in vacuo
  11. customThe crude material was purified on silica

出典と根拠

ORDレコード
ord-c725d48dfc3e4d78bb84dff78b894f3a
出典データセット
uspto-grants-2011_11
特許番号
US08067362B2

反応ノート

読み込み中…