Oxygen → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-(2-hydroxypropan-2-yl)-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

HRID 1482149노트

반응식

HRID 1482149 반응식
[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([C:42]([CH3:44])=[CH2:43])[C:38]2=[N:45][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:47])=[CH:28][C:29]=2[C:30]2[CH:46]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[O:54]=O>C(O)C.[Fe+2]>[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([C:42]([OH:54])([CH3:44])[CH3:43])[C:38]2=[N:45][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:47])=[CH:28][C:29]=2[C:30]2[CH:46]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 3

HCID 977OxygenHCID 4311764Sodium borohydride2회HCID 118316348Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(prop-1-en-2-yl)-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

생성물 1

HCID 118316385Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-(2-hydroxypropan-2-yl)-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

시약·촉매·용매 2

HCID 27284Ferrous cation촉매HCID 702Ethanol용매

실험 절차

Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(prop-1-en-2-yl)-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate (50 mg, 0.072 mmol, 1 equiv) was dissolved in ethanol (0.86 mL). To this solution was added iron(II) phthalacyanine (4.07 mg, 7.16 μmol, 0.1 equiv) and sodium borohydride (5.42 mg, 0.143 mmol, 2 equiv). The reaction was stirred under air for 1 hour. No reaction. The mixture was then placed under oxygen balloon and stirred for 2 hours. To this solution was added 10 mg catalyst and 10 mg sodium borohydride and stirred under the oxygen balloon again. It was found that the vial emitted heat and the solution of the reaction turned to dark purple and back to blue again. The reaction was stirred overnight. The reaction completed 30% by LCMS. It was used as is for the next reaction. LCMS (ESI, M+1): 716.4.

후처리

  1. customNo reaction
  2. stirringstirred for 2 hours
  3. temperatureemitted heat
  4. stirringThe reaction was stirred overnight
  5. customas is for the next reaction

출처 및 근거

ORD 기록
ord-0d7a41d4eb474f9187af7b48edfea057
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409922B2

반응 노트

불러오는 중…