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Water → 2-{[(Benzyloxy)carbonyl]amino}hexanedioic acid

HRID 326724
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HRID 326724 반응식
[CH2:1]([CH2:8][C:9]([OH:11])=[O:10])[CH2:2][C@H:3]([NH2:7])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.O.[CH2:20]([O:27][C:28](ON1C(=O)CCC1=O)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCOCC1>[CH2:20]([O:27][C:28]([NH:7][CH:3]([CH2:2][CH2:1][CH2:8][C:9]([OH:11])=[O:10])[C:4]([OH:6])=[O:5])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 92136L-2-Aminoadipic Acid

생성물 1

HCID 138764392-{[(Benzyloxy)carbonyl]amino}hexanedioic acid수율 106.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

A solution of L-2-aminoadipic acid (920 mg, 5.71 mmol), triethylamine (2.85 mL, 20.5 mmol) and water (3 mL) in 12 mL of dioxane was cooled to 0° C. and N-benzyloxycarbonyloxysuccinimide (Cbz-OSu: 1.71 g, 6.85 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours and at ambient temperature for 0.5 hours. The reaction mixture was washed with ethyl acetate and then acidified with aqueous potassium hydrogen sulfate. The acidic solution was extracted with ethyl acetate and the ethyl acetate solution was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 1.80 g of the title compound. MS (FAB+) m/e 296 (M+H)+.

후처리

  1. washThe reaction mixture was washed with ethyl acetate
  2. extractionThe acidic solution was extracted with ethyl acetate
  3. washthe ethyl acetate solution was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-cacd9f9a6d934fbf81753716232a4ea4
출처 데이터셋
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05270302

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