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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Methyl 1-amino-1-cyclopentanecarboxylate (H-Ac5c-OMe) → Methyl 1-({3-[(tert-butoxycarbonyl)amino]-2-phenylpropyl}amino)cyclopentanecarboxylate

HRID 1890721
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인쇄 미리보기

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HRID 1890721 반응식
O=[CH:2][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[NH2:19][C:20]1([C:25]([O:27][CH3:28])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[C:8]([O:7][C:6]([NH:5][CH2:4][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2][NH:19][C:20]1([C:25]([O:27][CH3:28])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:12])([CH3:11])([CH3:10])[CH3:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 231225Methyl 1-amino-1-cyclopentanecarboxylate (H-Ac5c-OMe)HCID 5049666Sodium triacetoxyborohydrideHCID 11414003tert-Butyl (3-oxo-2-phenylpropyl)carbamate

생성물 1

HCID 58550617Methyl 1-({3-[(tert-butoxycarbonyl)amino]-2-phenylpropyl}amino)cyclopentanecarboxylate

시약·촉매·용매 3

HCID 6212Chloroform용매
HCID 6344
Dichloromethane
용매
HCID 516892Sodium Bicarbonate용매

실험 절차

Into a solution of tert-butyl (3-oxo-2-phenylpropyl)carbamate from Step B (0.5 g, 2 mmol) in dry chloroform (20 mL) was added methyl 1-amino-1-cyclopentanecarboxylate (0.431 g, 3.01 mmol). After 15 minutes, sodium triacetoxyborohydride (0.893 g, 4.21 mmol) was added. After 4 hours of stirring at ambient temperature, the reaction mixture was diluted with DCM and 5% sodium bicarbonate. The layers were separated and the aqueous layer was extracted once with DCM. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to yield a residue, which was subjected to a normal phase chromatography, eluting with a gradient of 1-6% methanol in DCM. Concentration of the fractions containing the product provided the title compound. MS: m/z=377 (M+1).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted once with DCM
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a residue, which
  7. washeluting with a gradient of 1-6% methanol in DCM
  8. additionConcentration of the fractions containing the product

출처 및 근거

ORD 기록
ord-f2c4eb9b3f67496db16af66486442f38
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08507477B2

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