Diisopropylethylamine → (S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropylcarbamoyl)piperidine-1-carboxylate

HRID 600311노트

반응식

HRID 600311 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:51][C@:52]1([C:62]([O:64][CH3:65])=[O:63])[CH2:54][C@@H:53]1[C:55]1[CH:60]=[CH:59][C:58]([Br:61])=[CH:57][CH:56]=1>CN(C=O)C>[Br:61][C:58]1[CH:57]=[CH:56][C:55]([C@H:53]2[CH2:54][C@:52]2([NH:51][C:14]([C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:16])[C:62]([O:64][CH3:65])=[O:63])=[CH:60][CH:59]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 688617(2S)-1-((tert-butoxy)carbonyl)piperidine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67268087(1R,2R)-methyl 1-amino-2-(4-bromophenyl)cyclopropanecarboxylate hydrochloride

생성물 1

HCID 57999639(S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropylcarbamoyl)piperidine-1-carboxylate수율 34.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of (S)-1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (9.05 mg) in DMF (3 mL) was added Hunig's Base (0.019 mL) followed by HATU (15 mg). The mixture was allowed to stir at room temp for 10 min. To this solution was added in one portion (1R,2R)-methyl 1-amino-2-(4-bromophenyl)cyclopropanecarboxylate hydrochloride (11 mg) and the mixture was stirred overnight. The mixture was evaporated to dryness, the residue extracted into diethyl ether and washed well with water and brine, then dried over sodium sulfate. The sample was passed through a small silica plug/eluting with diethyl ether to give (S)-tert-butyl 2-((1R,2R)-2-(4-bromophenyl)-1-(methoxycarbonyl)cyclopropylcarbamoyl)piperidine-1-carboxylate (6 mg) as a colourless oil.

후처리

  1. stirringthe mixture was stirred overnight
  2. customThe mixture was evaporated to dryness
  3. extractionthe residue extracted into diethyl ether
  4. washwashed well with water and brine
  5. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-9164d3eae90649d6ad0938a7b9a3db49
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902181B2

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