Diisopropylethylamine → HCID 86757206, 화합물

HRID 1386920노트

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HRID 1386920 반응식
CC(C)(OC([N:7]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[C@H:8]1[C:19]([OH:21])=O)=O)C.Cl.[CH3:24][C:25]([O:28][C:29]([C@@H:31]1[CH2:47][S:46][S:45][CH2:44][C@H:43]([NH2:48])[C:42](=[O:49])[NH:41][CH2:40][CH2:39][C:34]2([CH2:38][CH2:37][CH2:36][CH2:35]2)[C:33](=[O:50])[NH:32]1)=[O:30])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH3:27][C:25]([O:28][C:29]([C@@H:31]1[CH2:47][S:46][S:45][CH2:44][C@H:43]([NH:48][C:19]([C@@H:8]2[C@@H:9]([C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)[CH2:10][CH2:11][NH:7]2)=[O:21])[C:42](=[O:49])[NH:41][CH2:40][CH2:39][C:34]2([CH2:35][CH2:36][CH2:37][CH2:38]2)[C:33](=[O:50])[NH:32]1)=[O:30])([CH3:24])[CH3:26]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9972479HCID 9972479, 화합물HCID 86757205HCID 86757205, 화합물

생성물 1

HCID 86757206HCID 86757206, 화합물수율 115.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To the mixture of (2S,3R)-1-[(1,1-dimethylethoxy)carbonyl]-3-(4-hydroxyphenyl)pyrolidine-2-carboxylic acid (46 mg, 0.15 mmol) and (8R,13R)-13-amino-6,14-dioxo-10,11-dithia-7,15-diazaspiro[4.12]heptadecane-8-carboxylic acid 1,1-dimethylethyl ester hydrochloride 70 mg, 0.15 mmol), prepared in Example 6, in 0.5 mL of DMF was added DIPEA (58 mg, 0.45 mmol) and HBTU (59 mg, 0.15 mmol). The solution was stirred at room temperature for 3 hours and was diluted with water to 3 mL. The resulting white precipitate was collected and was dried over night at reduced pressure to give 105 mg of (8R,13R)-13-[[[3(R)-(4-hydroxyphenyl)-2(S)-pyrrolidinyl]carbonyl]amino]-6,14-dioxo-10,11-dithia-7,15-diazaspiro[4.12]heptadecane-8-carboxylic acid 1,1-dimethylethyl ester as a white solid. This dried solid (85 mg) was the dissolved in 2 mL of dichloromethane and the solution was treated with 4 N HCl in dioxane (2 mL). The solution was stirred overnight and the solvent was then removed. The residue was purified by reversed-phase HPLC (5-95% of acetonitrile containing 0.75% of TFA in water oevr 40 min linear gradient) to give (8R,13R)-13-[[[3(R)-(4-hydroxyphenyl)-2(S)-pyrrolidinyl]carbonyl]amino]-6,14-dioxo-10,11-dithia-7,15-diazaspiro[4.12]heptadecane-8-carboxylic acid as a white solid (58 mg). HRMS (M+H): Obs. 551.2017, Calcd.551.1998.

후처리

  1. customThe resulting white precipitate was collected
  2. customwas dried over night at reduced pressure

출처 및 근거

ORD 기록
ord-24525d5152e447a2bae0a589c55b49c4
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265572B1

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