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

HRID 445004노트

반응식

HRID 445004 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-86b431910d2944ab983c16eef97dc21f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476228B2

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