Benzhydrylamine → BocLys(Fmoc) Benzhydrylamine

HRID 399700Notes

Reaction equation

HRID 399700 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C@H:16]([C:39]([OH:41])=[O:40])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][CH:26]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.CO.C(N(C(C)C)CC)(C)C.CN1C(=O)CCC1>[NH:15]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C@H:16]([C:39]([OH:41])=[O:40])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][CH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[C:38]1=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:23].[CH:1]([NH2:14])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 7036BenzhydrylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10983524(2S)-2-(((tert-butoxy)carbonyl)amino)-6-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid

Product 1

HCID 131720885BocLys(Fmoc) Benzhydrylamine

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent4×HCID 13387N-methyl-2-pyrrolidoneSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

Benzhydrylamine resin (3.0 g, 0.74 meq/g resin, 2.2 meq) was washed with 30 mL each of DCM, methanol (MeOH), DCM, 5% diisopropylethylamine (DIEA) in DCM (×2) DCM, and NMP (×2). BocLys(Fmoc) (1.14 g, 2.4 mmol), HBTU (0.91 g, 2.4 mmol), HOBt (0.37 g, 2.4 mmol) were dissolved in NMP (15 mL) to which was added NMM (0.51 mL, 3.63 mmol) and solution was preactivated for 5 minutes. This solution was added to the swelled resin and allowed to stir for 5 minutes. The resultant BocLys(Fmoc)-resin was washed with NMP (2×1 min) and DCM (3×1 min).

Workup

  1. additionThis solution was added to the swelled resin
  2. washThe resultant BocLys(Fmoc)-resin was washed with NMP (2×1 min) and DCM (3×1 min)

Sources & evidence

ORD record
ord-c352eed815dd4877a054493e6496ccb9
Source dataset
uspto-grants-1998_10
Patent number
US05824483

Reaction notes

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