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Diisopropylethylamine → 9H-fluoren-9-ylmethyl {2-[(4-{[(tert-butoxycarbonyl)amino]methyl}phenyl)amino]-2-oxoethyl}carbamate

HRID 1755201
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HRID 1755201 반응식
[C:1](NCC(O)=O)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].C(N(CC)C(C)C)(C)C.[NH2:32][CH2:33][C:34]([NH:36][C:37]1[CH:51]=[CH:50][C:40]([CH2:41][NH:42][C:43](=[O:49])[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:39][CH:38]=1)=[O:35]>CN(C=O)C>[C:45]([O:44][C:43]([NH:42][CH2:41][C:40]1[CH:39]=[CH:38][C:37]([NH:36][C:34](=[O:35])[CH2:33][NH:32][C:1](=[O:2])[O:3][CH2:4][CH:5]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]3[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=3)=[CH:51][CH:50]=1)=[O:49])([CH3:46])([CH3:47])[CH3:48]
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 93124Fmoc-Gly-OHHCID 86718402Tert-butyl [4-(glycylamino)benzyl]carbamate

생성물 1

HCID 867184019H-fluoren-9-ylmethyl {2-[(4-{[(tert-butoxycarbonyl)amino]methyl}phenyl)amino]-2-oxoethyl}carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

To a solution of Fmoc-Glycine (16 g, 54 mmol, 1.0 eq.) in dry DMF (160 mL) at 0° C. was added N,N-diisopropylethylamine (14 g, 108 mmol, 2.0 eq) and N N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (16 g, 54 mmol, 1.0 eq). The mixture was stirred at 0° C. for 30 min and a solution of tert-butyl [4-(glycylamino)benzyl]carbamate (12 g, 54 mmol, 1.0 eq.) in dry DMF (50 mL) was added. The mixture was stirred at room temperature overnight poured into ice water (400 mL) and extracted with EtOAc (400 mL×2). The organic layer was washed with brine (200 mL×2), dried over Na2SO4 and concentrated in vacuum. The residue was re-crystallized from EtOAc (200 mL) and petroleum ether (400 mL) to afford #B118 (18 g, 66.6%) as a white solid. 1H NMR (400 Hz, DMSO-d6): δ 9.93 (s, 1H), 7.91 (d, 2H), 7.75 (d, 2H), 7.61 (m, 1H), 7.52 (d, 2H), 7.43 (m, 2H), 7.36 (m, 3H), 7.18 (d, 3H), 4.32 (d, 2H), 4.26 (m, 1H), 4.07 (d, 2H), 3.80 (d, 2H), 1.39 (s, 9H)

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. extractionextracted with EtOAc (400 mL×2)
  3. washThe organic layer was washed with brine (200 mL×2)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customThe residue was re-crystallized from EtOAc (200 mL) and petroleum ether (400 mL)
  7. customto afford #B118 (18 g, 66.6%) as a white solid

출처 및 근거

ORD 기록
ord-c8b3a153a0b54dc0960b8e7dd14fc917
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09169264B2

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