Triethylamine → HCID 57968648, 화합물

HRID 882768노트

반응식

HRID 882768 반응식
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]3[CH2:18][C@H:17]([O:19][C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[CH2:16][NH:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C1COCC1>[CH3:34][S:35]([N:15]1[CH2:16][C@@H:17]([O:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH2:18][C@H:14]1[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][N:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)[CH2:6][CH2:7]1)=[O:13])(=[O:37])=[O:36]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44601159HCID 44601159, 화합물

생성물 1

HCID 57968648HCID 57968648, 화합물수율 88.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice-cooled solution of (2S,4S)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-(4-fluoro-phenoxy)-pyrrolidine (29 mg, 0.08 mmol) in THF (0.8 mL) with Et3N (60 μL, 0.4 mmol) was added methanesulfonyl chloride (19 μL, 0.24 mmol). The reaction mixture was allowed to warm to rt and was stirred for 18 h. The mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2 (3×). The combined organic layers were dried and concentrated. Purification by FCC provided the desired product (31 mg, 87%). MS (ESI): mass calcd. for C21H30FN3O4S, 439.19; m/z found, 440.5 [M+H]+. 1H NMR (CDCl3): 7.00-6.94 (m, 2H), 6.83-6.78 (m, 2H), 4.94-4.89 (m, 1H), 4.86 (ddd, J=8.8, 4.4, 4.4 Hz, 1H), 4.10-4.03 (m, 1H), 3.78-3.40 (m, 5H), 3.08 (d, J=4.0 Hz, 3H), 2.84 (dd, J=16.2, 7.8 Hz, 1H), 2.75-2.66 (m, 1H), 2.57-2.26 (m, 4H), 2.25-2.14 (m, 1H), 2.07-1.97 (m, 2H), 1.97-1.71 (m, 4H), 1.69-1.55 (m, 2H).

후처리

  1. additionThe mixture was diluted with satd
  2. extractionaq. NaHCO3 and extracted with CH2Cl2 (3×)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customPurification by FCC

출처 및 근거

ORD 기록
ord-1fc13af27cd5413eb34c32334bf3b8e6
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236792B2

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