Diisopropylamine → 9-Methylene-9H-fluorene

HRID 842410

반응식

HRID 842410 반응식
CC1C=CC(C(N)C2C=CC=CC=2)=CC=1.[CH:16]1[C:28]2[CH:27]([CH2:29]OC(N[C@H](C(NC(B3OC(CCC(C)CC(O)=O)(C)C(C)(C)O3)CC)=O)CC(C)C)=O)[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(NC(C)C)(C)C.C(OC(=O)C)(=O)C.CN1CCOCC1>CN(C)C=O>[CH2:29]=[C:27]1[C:28]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]2[C:26]1=[CH:25][CH:24]=[CH:23][CH:22]=2

참가 물질

8

반응물 6

HCID 7912DiisopropylamineHCID 7918Acetic Anhydride2회HCID 79724-Methylmorpholine2회HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27342954-MethylbenzhydrylamineHCID 229420655-[2-[1 (RS)-[[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]amino]propyl]-4(RS),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvaleric acid

생성물 1

HCID 781479-Methylene-9H-fluorene

시약·촉매·용매 1

HCID 6228Dimethylformamide용매4회

실험 절차

5 g (5.25 mmol) of 4-methylbenzhydrylamine resin were swollen in dimethylformamide and excess solvent was drained from the resin. The resin was then resuspended in dimethylformamide containing 3.4 g (5.48 mmol) of 5-[2-[1(RS)-[[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]amino]propyl]-4(RS),5,5-trimethyl-1,3,2-dioxaborolan-4-yl]-3(RS)-methylvaleric acid and 3 g (8.2 mmol) of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate. Thereto were added 3.0 ml (16.5 mmol) of diisopropylamine. The resulting mixture was agitated for 100 minutes and the resin was then drained and washed three times with dimethylformamide. The resin was then resuspended in dimethylformamide containing 5 ml (54.8 mmol) of acetic anhydride and 11.5 ml (110 mmol) of N-methylmorpholine. The mixture was agitated for 30 minutes and the resin was then drained. The resin was then resuspended in dimethylformamide containing 5 ml (54.8 mmol) of acetic anhydride and 11.5 ml (110 mmol) of N-methylmorpholine. The mixture was agitated for 30 minutes and the resin was then drained and washed three times with dimethylformamide, twice with ethyl acetate, twice with dichloromethane and twice with diethyl ether and then dried under a vacuum. After drying there was obtained 6 g of 5-[2-[1(RS)-[[N-[(9-fluorenyl)methoxycarbonyl]-L-leucyl]amino]propyl]-4-(RS),5,5-trimethyl-1,3 ,2-dioxoborolan-4-yl]-3(RS)-methyl-N-(RS)-(4-methylphenyl)-benzyl]valeramide-polystyrene conjugate as a pale brown solid (0.25 mmol/g loading estimated by quantitation of dibenzofulvene at 301 nM).

후처리

  1. washwashed three times with dimethylformamide
  2. stirringThe mixture was agitated for 30 minutes
  3. stirringThe mixture was agitated for 30 minutes
  4. washwashed three times with dimethylformamide
  5. dry with materialtwice with ethyl acetate, twice with dichloromethane and twice with diethyl ether and then dried under a vacuum
  6. customAfter drying there

출처 및 근거

ORD 기록
ord-3b50589ce1024e90b7afad10eaf0d5d5
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372883B1

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