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Triethylamine → (2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-chloro-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester

HRID 1068074
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HRID 1068074 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[C:12]([O:16][C:17](=[O:37])[C@@H:18]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24][C@H:25]([OH:28])[CH2:26][Cl:27])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:12]([O:16][C:17](=[O:37])[C@@H:18]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:19][CH2:20][CH2:21][CH2:22][N:23]([C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])[CH2:24][C@H:25]([OH:28])[CH2:26][Cl:27])([CH3:15])([CH3:14])[CH3:13]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 10810670(2S,9S)-2-[(tert-Butoxycarbonyl)amino]-10-chloro-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester

생성물 1

HCID 10792289(2S,9S)-2-[(tert-Butoxycarbonyl)amino]-7-(carbobenzyloxy)-10-chloro-9-hydroxy-7-azadecanoic Acid tert-Butyl Ester수율 93.1%

시약·촉매·용매 1

HCID 6212
Chloroform
용매
3회

실험 절차

A solution of benzyl chloroformate (1.21 g, 7.09 mmol) in chloroform (10 mL) was added over a period of 15 min to an ice-cold solution of 12a (2.16 g, 5.46 mmol) in chloroform (40 mL) under an Ar atmosphere. After dropwise addition of triethylamine (1.11 g, 11.0 mmol) in chloroform (10 mL), the reaction mixture was stirred for 4.5 hours at rt. The reaction mixture was extracted with 1 N HCl (60 mL) and water (60 mL), dried, and concentrated. The residue was purified by flash chromatography (33% ethyl acetate/hexane) to give 13a (2.69 g, 93%) as a colorless oil: 1H NMR 61.30-1.83 (m, 6H), 1.44 (s, 9H), 1.45 (s, 9H), 3.20-3.64 (m, 6H), 3.93 (dd, 1H, J=8.2; 5.5), 4.00 (m, 1H), 5.12 (s, 2H), 7.26-7.40 (m, 5H); 13C NMR δ 24.1, 28.3, 28.8, 32.5, 49.4, 51.4, 52.2, 55.7, 68.4, 71.0, 80.4, 82.5, 129.0, 129.1, 129.6, 138.0, 157.5-158.4 (br), 158.1, 173.7; HRMS m/z calcd for C26H42ClN2O7 529.2681, found 529.2694. Anal. calcd. for C26H41ClN2O7: C 59.03, H 7.81, N 5.29. Found: C 59.09, H 7.78, N 5.21. [α]23D−21.8° (c 1.00, CH3OH).

후처리

  1. extractionThe reaction mixture was extracted with 1 N HCl (60 mL) and water (60 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (33% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0c6b9ff0f5754d428b15d2428fa82a44
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06248866B1

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