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Water → (R)-2-(2-(tert-Butoxycarbonylamino)-2-methylpropanamido)-4-phenylbutanoic acid

HRID 1036737
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HRID 1036737 반응식
O=C1CCC(=O)N1[C:8](=[O:20])[C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH3:10].[CH:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C@@H:29]([NH2:33])[C:30]([OH:32])=[O:31])=[CH:23][CH:22]=1.O.C(N(CC)CC)C>C1COCC1>[C:15]([O:14][C:13]([NH:12][C:9]([CH3:11])([CH3:10])[C:8]([NH:33][C@H:29]([CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][CH:21]=[CH:26][CH:25]=1)[C:30]([OH:32])=[O:31])=[O:20])=[O:19])([CH3:18])([CH3:17])[CH3:16]
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참가 물질

6

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HCID 962WaterHCID 8471TriethylamineHCID 6950302D-HomophenylalanineHCID 71060486Tert-butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-methyl-1-oxopropan-2-ylcarbamate

생성물 1

HCID 22862434(R)-2-(2-(tert-Butoxycarbonylamino)-2-methylpropanamido)-4-phenylbutanoic acid

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
50 °C

실험 절차

A mixture comprising of tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-methyl-1-oxopropan-2-ylcarbamate (1 g, 3.52 mmol) (prepared according to the procedure described in EP1486498A1 page 20) and H-D-Homophe-OH (0.630 g, 3.52 mmol) in THF (16 ml)/water (4 ml) was treated with triethylamine (1.471 ml, 10.55 mmol). The reaction mixture was stirred at 50° C. for 9 hours. THF was removed in vacuo. The aqueous solution was further diluted with water and the pH adjusted to pH 2-3 using 1M HCl. The resulting aqueous phase was extracted with EtOAc. The organic portion was dried (MgSO4) and concentrated in vacuo to afford the title compound.

후처리

  1. customTHF was removed in vacuo
  2. additionThe aqueous solution was further diluted with water
  3. extractionThe resulting aqueous phase was extracted with EtOAc
  4. dry with materialThe organic portion was dried (MgSO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-dc4a3cf71c9c482baed69d543722a3d6
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546416B2

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