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Triethylamine → (3-Cyano-5-oxo-6-phenyl-hexahydro-pyrrolo[2,1-b]thiazol-6-yl)-carbamic acid tert-butyl ester

HRID 507442
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HRID 507442 반응식
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15](=[O:16])[N:14]2[CH:10]([S:11][CH2:12][CH:13]2[C:17](=O)[NH2:18])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15](=[O:16])[N:14]2[CH:10]([S:11][CH2:12][CH:13]2[C:17]#[N:18])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 68466014HCID 68466014, 화합물

생성물 1

HCID 57443731(3-Cyano-5-oxo-6-phenyl-hexahydro-pyrrolo[2,1-b]thiazol-6-yl)-carbamic acid tert-butyl ester수율 83.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of compound 17 (380 mg, 1.0 mmol) in CH2Cl2 (50 mL) was added TFAA (252 uL, 1.2 mmol) dropwise at room temperature, followed by the addition of Et3N (404 mg, 4 mmol). After stirring for 1 h, the mixture was washed with brine, dried over Na2SO4. After concentration, the residue was purified by column chromatography on silica gel (PE: EA=15:1) to give compound 18 (300 mg, 83.6%). 1 H NMR (400 MHz, CDCl3) δ 1.40 (s, 9 H), 3.26-3.27 (m, 1 H), 3.30-3.31 (m, 1 H), 3.31-3.34 (m, 1 H), 3.43-3.47 (m, 1 H), 5.06 (bs, 1 H), 5.22 (bs, 1H), 5.50 (bs, 1H), 7.37-7.49 (m, 5H). MS (M+1): 360.

후처리

  1. washthe mixture was washed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationAfter concentration
  4. customthe residue was purified by column chromatography on silica gel (PE: EA=15:1)

출처 및 근거

ORD 기록
ord-bff966e037a74ae699d0d5493770a69a
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786163B2

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