Ammonium formate → (15R,19R)-tert-butyl 15-amino-19-(decylcarbamoyloxy)-14,22-dioxo-4,7,10,21-tetraoxa-17-thia-13,23-diazatritriacontan-1-oate

HRID 2407954노트

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HRID 2407954 반응식
C(OC([NH:11][C@@H:12]([CH2:34][S:35][CH2:36][C@H:37]([O:53][C:54](=[O:66])[NH:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH2:38][O:39][C:40](=[O:52])[NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:13](=[O:33])[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=O)C1C=CC=CC=1.C([O-])=O.[NH4+].CO.O>CO.[Pd]>[NH2:11][C@@H:12]([CH2:34][S:35][CH2:36][C@H:37]([O:53][C:54](=[O:66])[NH:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH2:38][O:39][C:40](=[O:52])[NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:13](=[O:33])[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]

참가 물질

6

반응물 3

HCID 2723923Ammonium formateHCID 22242641Methanol--water (1/1)HCID 86678324(15R,19R)-tert-butyl15-(benzyloxycarbonylamino)-19-(decylcarbamoyloxy)-14,22-dioxo-4,7,10,21-tetraoxa-17-thia-13,23-diazatritriacontan-1-oate

생성물 1

HCID 86678323(15R,19R)-tert-butyl 15-amino-19-(decylcarbamoyloxy)-14,22-dioxo-4,7,10,21-tetraoxa-17-thia-13,23-diazatritriacontan-1-oate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
40 °C

실험 절차

A solution of (15R,19R)-tert-butyl 15-(benzyloxycarbonylamino)-19-(decylcarbamoyloxy)-14,22-dioxo-4,7,10,21-tetraoxa-17-thia-13,23-diazatritriacontan-1-oate in MeOH (0.1 M) was stirred under nitrogen at room temperature. A small scoop (catalytic) of Pd/C was then added and stirred. A solution of ammonium formate (8 eq) in 9:1 MeOH/water was then added, the reaction vessel purged with nitrogen and heated to 40° C. for 4 hours. The reaction was then cooled to room temperature and diluted with EtOAc. The reaction mixture was filtered through celite then Na2SO4 and concentrated to afford the title compound as a light yellow oil. The concentrated material was used with no further purification.

후처리

  1. customthe reaction vessel purged with nitrogen
  2. temperatureThe reaction was then cooled to room temperature
  3. additiondiluted with EtOAc
  4. filtrationThe reaction mixture was filtered through celite
  5. concentrationNa2SO4 and concentrated

출처 및 근거

ORD 기록
ord-acf7c7837ba442cd88e122a3c558d4b3
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08808703B2

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