2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 117598746, 화합물

HRID 522414노트

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HRID 522414 반응식
FC(F)(F)[C:3]([O-:5])=[O:4].[CH:8]1([C@H:14]2[C:47](=[O:48])[N:46]3[CH2:49][C@@H:43]([CH2:44][C@H:45]3[C:50](=[O:67])[NH:51][C@:52]3([C:57](=[O:66])[NH:58][S:59]([C:62]4([CH3:65])[CH2:64][CH2:63]4)(=[O:61])=[O:60])[CH2:54][C@H:53]3[CH:55]=[CH2:56])[O:42][C:26]3=[N:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=4[C:34]([O:35][CH:36]4[CH2:41][CH2:40][NH2+:39][CH2:38][CH2:37]4)=[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[CH2:68][C@H:18]3[O:17][C:16](=[O:69])[NH:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CCN(C(C)C)C(C)C.FC(F)(F)S(O[CH2:85][C:86]([F:89])([F:88])[F:87])(=O)=O>C(#N)C>[CH:3]([O-:5])=[O:4].[CH:8]1([C@H:14]2[C:47](=[O:48])[N:46]3[CH2:49][C@@H:43]([CH2:44][C@H:45]3[C:50](=[O:67])[NH:51][C@:52]3([C:57](=[O:66])[NH:58][S:59]([C:62]4([CH3:65])[CH2:63][CH2:64]4)(=[O:61])=[O:60])[CH2:54][C@H:53]3[CH:55]=[CH2:56])[O:42][C:26]3=[N:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=4[C:34]([O:35][CH:36]4[CH2:37][CH2:38][NH+:39]([CH2:85][C:86]([F:89])([F:88])[F:87])[CH2:40][CH2:41]4)=[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[CH2:68][C@H:18]3[O:17][C:16](=[O:69])[NH:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

참가 물질

5

반응물 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 117598881HCID 117598881, 화합물

생성물 1

HCID 117598746HCID 117598746, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
55 °C

실험 절차

To a solution of the product from Step 1 (101 mg, 0.102 mmol) in acetonitrile (5 mL) was added Hunig's base (0.089 mL, 0.511 mmol) followed by 2,2,2-trifluoroethyl trifluoromethanesulfonate (71.1 mg, 0.306 mmol). The reaction was stirred at 55° C. for 3 hours after which it was quenched with water and extracted with EtOAc. Purification by PTLC (3% MeOH in CH2Cl2) followed by reverse phase HPLC (0 to 90% acetonitrile in water; with 0.1% HCOOH) provided the title compound.

후처리

  1. customwas quenched with water
  2. extractionextracted with EtOAc
  3. customPurification by PTLC (3% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-842ed8e2b6ee423bbe89887b2c74b90e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328138B2

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