Benzhydrylamine → HCID 178427601, compound

HRID 1731708Notes

Reaction equation

HRID 1731708 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:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:16]([C:34]([OH:36])=[O:35])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:33])[NH:22][S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C1CCC(N=C=NC2CCCCC2)CC1.C(N(C(C)C)CC)(C)C.N[C@H](C(O)=O)CCCNC(=N)N.CC(OC(C)=O)=O.N1C=CC=CC=1>CN(C)C=O.C(Cl)Cl>[NH:15]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:16]([C:34]([OH:36])=[O:35])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:33])[NH:22][S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24].[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

9

Reactant 6

HCID 7036BenzhydrylamineHCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 83767L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methylphenyl)sulfonyl]amino]methyl]-HCID 22348678Acetic anhydride pyridineHCID 178418600HCID 178418600, compound

Product 1

HCID 178427601HCID 178427601, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Benzhydrylamine-resin (BHA) (40.44 g, 0.5 mmol/g, 20.22 mmol) was coupled with Boc-Arg(Tos)-OH (34.6 g, 80.7 mmol) in 25% dimethylformamide:methylene chloride [DMF-CH2Cl2 ] (250 ml) with DCC (16.78 g, 81.4 mmol) for 2 hours followed by the addition of 1% diisopropylethylamine and reacted for 0.5 hour longer. The resultant Boc-Arg(Tos)-BHA-resin was washed with CH2Cl2 (3×250 ml), MeOH (3×250 ml), CH2Cl2 (3×250 ml) and dried. The coupling and washing procedures were repeated and an aliquot was hydrolyzed (1 ml of 6M propionic/HCl at 130° C. for 2 hours). Amino acid analysis showed a substitution of 0.35 mmol of Arg per gram of resin. The remaining amino groups were acetylated with Ac2O-pyridine yield: 48.88 g.

Workup

  1. customreacted for 0.5 hour longer
  2. washThe resultant Boc-Arg(Tos)-BHA-resin was washed with CH2Cl2 (3×250 ml), MeOH (3×250 ml), CH2Cl2 (3×250 ml)
  3. customdried
  4. washThe coupling and washing procedures
  5. custom(1 ml of 6M propionic/HCl at 130° C. for 2 hours)

Sources & evidence

ORD record
ord-1891bb62ab154eee8fb2861a008e7a97
Source dataset
uspto-grants-1986_11
Patent number
US04622312

Reaction notes

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