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Diisopropylethylamine → 5-{9-[(s)-1-Tert-butoxycarbonyl-3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-propylcarbamoyl]-nonyloxy}-isophthalic acid di-tert-butyl ester

HRID 1022420
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HRID 1022420 반응식
[C:1]([O:5][C:6](=[O:46])[C:7]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:45])[NH:31][C@H:32]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:60]1[C:65](=[O:66])[CH2:64][CH2:63][C:61]1=[O:62])=[N+](C)C)C.CCN(C(C)C)C(C)C>C1COCC1>[C:13]([O:12][C:10](=[O:11])[C:9]1[CH:17]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:45])[NH:31][C@H:32]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:33][CH2:34][C:35]([O:37][N:60]2[C:65](=[O:66])[CH2:64][CH2:63][C:61]2=[O:62])=[O:36])[CH:19]=[C:7]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:46])[CH:8]=1)([CH3:16])([CH3:15])[CH3:14]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate2회HCID 68443966HCID 68443966, 화합물

생성물 1

HCID 874559205-{9-[(s)-1-Tert-butoxycarbonyl-3-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-propylcarbamoyl]-nonyloxy}-isophthalic acid di-tert-butyl ester

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

5-[9-((S)-1-tert-Butoxycarbonyl-3-carboxy-propylcarbamoyl)-nonyloxy]-isophthalic acid di-tert-butyl ester (70 mg, 0.11 mmol) was dissolved in dry THF (1 ml). TSTU (40 mg, 0.13 mmol) and DIPEA (0.05 ml) was added. The mixture was stirred at room temperature under nitrogen over the weekend. The mixture was concentrated. The residue was redissolved in EtOAc and filtered. The filtrate was washed with 0.1N HCl (2×), washed with brine (1×), dried (Na2SO4) and concentrated to give a clear syrup. There was still starting material present and the TSTU-treatment was repeated followed by work up to give the title compound as a clear syrup.

후처리

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was redissolved in EtOAc
  3. filtrationfiltered
  4. washThe filtrate was washed with 0.1N HCl (2×)
  5. washwashed with brine (1×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customto give a clear syrup

출처 및 근거

ORD 기록
ord-5f55972c60ad40db876a1df4a68ce6b1
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722620B2

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