Glycine → HCID 178427602, compound

HRID 2231815Notes

Reaction equation

HRID 2231815 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])CCCNC(=N)N.NCC(O)=O.[C:18]([NH:25][C@H:26]([C:44]([OH:46])=[O:45])[CH2:27][CH2:28][CH2:29][NH:30][C:31](=[NH:43])[NH:32][S:33]([C:36]1[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=1)(=[O:35])=[O:34])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C=O)C.C(Cl)Cl>[C:18]([NH:25][C@H:26]([C:44]([OH:46])=[O:45])[CH2:27][CH2:28][CH2:29][NH:30][C:31](=[NH:43])[NH:32][S:33]([C:36]1[CH:37]=[CH:38][C:39]([CH3:40])=[CH:41][CH:42]=1)(=[O:34])=[O:35])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[NH2:1][CH2:2][C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 750Glycine2×HCID 10868DicyclohexylcarbodiimideHCID 83767L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methylphenyl)sulfonyl]amino]methyl]-HCID 178418600HCID 178418600, compound

Product 1

HCID 178427602HCID 178427602, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Condensation with arginine and BOC-deprotection. The Gly-resin is suspended in 200 ml of methylene chloride and treated with a triple-molar quantity respect to the glycine of the second amino acid (first amino acid of the sequence desired), adding a solution of 9.85 g (23 mmol) of BOC-Nω -tosyl-L-arginine in 60 ml of DMF:CH2Cl2 1:1. After 10 minutes under agitation, 4.76 g (23 mmol) of DCCD dissolved in 30 ml of methylene chloride are added and left under agitation at room temperature for 20 hours. The resin is then filtered and washed with CH2Cl2 and with ethanol, then vacuum-dried obtaining 12.3 g of BOC-Nω -tosyl-L-arginine-glycine-resin which, when controlling with ninhydrin, confirms the absence of free amine groups.

Workup

  1. additionare added
  2. filtrationThe resin is then filtered
  3. washwashed with CH2Cl2 and with ethanol
  4. customvacuum-dried

Sources & evidence

ORD record
ord-120052bb8202415e8454131e383cb1ed
Source dataset
uspto-grants-1988_11
Patent number
US04784988

Reaction notes

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