Methanesulfonic Acid → HCID 178463685, compound

HRID 529431Notes

Reaction equation

HRID 529431 reaction equation
[N:1]1([C:18]([O:20]C(C)(C)C)=O)[CH2:17][CH2:16][CH2:15][C@H:2]1[C:3]([N:5]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:6][CH3:7])=[O:4].[NH:25]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C@H:26](C(O)=O)[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].CS(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1>[NH:25]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C@H:26]([C:18]([N:1]1[CH2:17][CH2:16][CH2:15][C@H:2]1[C:3]([N:5]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:6][CH3:7])=[O:4])=[O:20])[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]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 83767L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methylphenyl)sulfonyl]amino]methyl]-HCID 110677859Boc-Pro-NEtBn

Product 1

HCID 178463685HCID 178463685, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Boc-Arg(Ts)-Pro-NEtBn was prepared by a similar procedure to Example 1 from Boc-Pro-NEtBn and Boc-Arg(Ts). To the solution composed of the compound (1.00 g), chlorobenzene (5.8 ml) and DBF (1.5 ml), methanesulfonic acid (1.41 g, 9.8 equivalents) was added at room temperature, and the resulting mixture was stirred at room temperature for 24 hours, thereby the Boc group was removed (reaction conversion ratio: 100.0%). After the reaction, 10% aqueous sodium carbonate solution (12 ml) was added thereto, and the resulting mixture was stirred for 15 minutes for neutralization. Then, the aqueous layer was separated off, thereby a solution containing Arg(Ts)-Pro-NEtBn (8.58 g) was obtained.

Workup

  1. additionwas added at room temperature
  2. customthe Boc group was removed
  3. custom(reaction conversion ratio: 100.0%)
  4. additionwas added
  5. stirringthe resulting mixture was stirred for 15 minutes for neutralization
  6. customThen, the aqueous layer was separated off
  7. additiona solution containing Arg(Ts)-Pro-NEtBn (8.58 g)
  8. customwas obtained

Sources & evidence

ORD record
ord-18bad930b030448ab38298c2d737e1d2
Source dataset
uspto-grants-2016_05
Patent number
US09346850B2

Reaction notes

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