4-Methylmorpholine → 9-Methylene-9H-fluorene

HRID 850871

Reaction equation

HRID 850871 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14]OC(N[C@H](C(O)=O)CC3C=CC=CC=3C)=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH2:14]=[C:12]1[C:13]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2761469(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-methylphenyl)propanoic acid

Product 1

HCID 781479-Methylene-9H-fluorene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3.2 g (8.1 mmol) of N-[(9-fluorenyl)methoxycarbonyl]-3-(2-methylphenyl)-L-alanine and 2.17 g (6.75 mmol) of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate in 22 ml of dimethylformamide was added to the resin from paragraph viii) and subsequently 1.5 ml (13.5 mmol) of N-methylmorpholine were added. The mixture was agitated for 30 minutes and then the resin was drained and washed five times with 30 ml of dimethylformamide, twice with 30 ml of dichloromethane, twice with 30 ml of ethyl acetate and twice with 30 ml of diethyl ether. After drying there were obtained 8.95 g of 5-[4-[[N-[N-[N-[(9-fluorenyl)methoxycarbonyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]-N-[3,3,3-trifluoro-1(RS)-(dimethoxymethyl)propyl]amino]methyl]-3,5-dimethoxyphenoxy]-N-(4-methyl-α-(RS)-phenylbenzyl)valeramide-polystyrene conjugate as a pale brown solid (0.31 mmol/g loading estimated by quantitation of dibenzofulvene at 301 nm).

Workup

  1. additionwere added
  2. washwashed five times with 30 ml of dimethylformamide
  3. customAfter drying there

Sources & evidence

ORD record
ord-0cc918badc274e2b914893eb67b690cf
Source dataset
uspto-grants-2000_01
Patent number
US06018020

Linked notes

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