Trifluoroacetic acid → HCID 25152743, 화합물

HRID 539139노트

반응식

HRID 539139 반응식
[OH:1][C@H:2]1[CH2:17][C:16](=[O:18])[O:15][O:14][C@H:13](/[CH:19]=[CH:20]/[CH2:21][CH2:22][S:23]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:12][C:11](=[O:43])[NH:10][C@H:9]([CH:44]([CH3:46])[CH3:45])[C:8](=[O:47])[NH:7][C@H:6]([CH3:48])[C:5](=[O:49])[NH:4][C@@H:3]1[CH:50]([CH3:52])[CH3:51].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][C@H:2]1[CH2:17][C:16](=[O:18])[O:15][O:14][C@H:13](/[CH:19]=[CH:20]/[CH2:21][CH2:22][SH:23])[CH2:12][C:11](=[O:43])[NH:10][C@H:9]([CH:44]([CH3:46])[CH3:45])[C:8](=[O:47])[NH:7][C@H:6]([CH3:48])[C:5](=[O:49])[NH:4][C@@H:3]1[CH:50]([CH3:52])[CH3:51]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86639580HCID 86639580, 화합물

생성물 1

HCID 25152743HCID 25152743, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 9 (24.7 mg, 0.035 mmol) in CH2Cl2 (1.4 mL) was added triethylsilane (28 μL, 0.175 mmol) followed by the dropwise addition of TFA (0.35 mL, 25% v/v). After stirring for 1 h the reaction mixture was concentrated in vacuo and put under high vacuum for 2 h to give the crude thiol 10. At 0° C. to a solution of thiol 10 in CH2Cl2 (0.45 mL) was added diisopropylethylamine (30 μL, 0.172 mmol) followed by acetyl chloride (2.43 μL, 0.034 mmol) in CH2Cl2 (0.1 mL). After stirring for 2 h 10 min 1M HCl (1 mL) was added followed by EtOAc (10 mL) the layers were separated and the organic layer was washed with sat. brine (10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography (eluent 1:0-98:2-96:4-94:6-92.8 CH2Cl2/MeOH) gave the product 11 (7.3 mg, 0.014 mmol, 41%) as a white solid: Rf 0.47 MeOH/CH2Cl2 (1:9).

후처리

  1. concentrationwas concentrated in vacuo
  2. waitput under high vacuum for 2 h

출처 및 근거

ORD 기록
ord-eff13ef88a504e018cc3ab26816edf0f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865655B2

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