Diisopropylethylamine → Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-D-norleucylglycinate

HRID 730832

반응식

HRID 730832 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][C@@H:5]([NH:9][C:10]([O:12][CH2:13][CH:14]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[C:6]([OH:8])=O.N=C=N.Cl.[CH3:31][O:32][C:33](=[O:36])[CH2:34][NH2:35].C1C=NC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH:16]1[C:15]2[CH:14]([CH2:13][O:12][C:10]([NH:9][C@@H:5]([C:6]([NH:35][CH2:34][C:33]([O:32][CH3:31])=[O:36])=[O:8])[CH2:4][CH2:3][CH2:2][CH3:1])=[O:11])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 160435CarbodiimideHCID 181649HOAtHCID 2756111(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid

생성물 1

HCID 67401200Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-D-norleucylglycinate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of fmoc-D-Nle-OH (10 g, 28.3 mmol, Novabiochem) and PS-carbodiimide (33 g, 42.45 mmol, 1.28 mmol/g, Argonaut Technologies Inc.) in dichloromethane (250 mL) was stirred at room temperature for 0.5 h. Then, glycine methyl ester hydrochloride (5.3 g, 42.45 mmol, Aldrich), HOAt (3.8 g, 28.3 mmol, Perseptive Biosystems) and diisopropylethylamine (16 mL, 84.9 mmol, Aldrich) were added and the mixture was stirred at room temperature for 16 h. The mixture was filtered and the resin was washed with dichloromethane (2×70 mL). The filtrate was concentrated in vacuo and the residue was purified by column chromatography, eluting with EtOAc/hexane (1:2) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 425 (M+1).

후처리

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. filtrationThe mixture was filtered
  3. washthe resin was washed with dichloromethane (2×70 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by column chromatography
  6. washeluting with EtOAc/hexane (1:2)

출처 및 근거

ORD 기록
ord-82221a597aeb4b0184ba9efcc11632d3
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582761B2

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