Methanesulfonic Acid → HCID 178465174, compound

HRID 529427

Reaction equation

HRID 529427 reaction equation
[NH:1]([C:32](OC(C)(C)C)=[O:33])[C@H:2]([C:20]([N:22]1[CH2:31][CH2:30][CH2:29][C@H:23]1[C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[NH:39]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[C@H:40](C(O)=O)[CH2:41][CH:42]([CH3:44])[CH3:43].CS(O)(=O)=O.N(C(OC(C)(C)C)=O)[C@@H](C(O)=O)CC(C)C.C1C=C2N=NN(O)C2=CC=1.O.N[C@H](C(N[C@H](C(N1CCC[C@H]1C(NCC)=O)=O)CCCNC(=N)NS(C1C=CC(C)=CC=1)(=O)=O)=O)CC(C)C.CCN=C=NCCCN(C)C.Cl>ClCCl.C(N(CC)CC)C>[NH:39]([C:48]([O:50][C:51]([CH3:53])([CH3:52])[CH3:54])=[O:49])[C@H:40]([C:32]([NH:1][C@H:2]([C:20]([N:22]1[CH2:31][CH2:30][CH2:29][C@H:23]1[C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[O:21])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:19])[NH:8][S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10])=[O:33])[CH2:41][CH:42]([CH3:44])[CH3:43]

Participants

10

Reactant 7

HCID 6395Methanesulfonic Acid2×HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 637604tert-Butoxycarbonyl-D-leucineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 178465175HCID 178465175, compoundHCID 178465176HCID 178465176, compound

Product 1

HCID 178465174HCID 178465174, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Boc-Leu-Arg(Ts)-Pro-NHEt was prepared from Boc-Arg(Ts)-Pro-NHEt obtained in Example 1 and Boc-Leu by the same procedure as Example 1. To a solution composed of the compound (0.969 g) and dichloromethane (10 ml), methanesulfonic acid (0.78 g) was added at room temperature, and the resulting mixture was stirred at room temperature for 4 hours, thereby the Boc group was removed (reaction conversion ratio: 100.0%). After the reaction, triethylamine in an amount of the same molar equivalent as that of the added methanesulfonic acid was added thereto, and the resulting mixture was stirred for 15 minutes. After Boc-D-Leu (0.40 g) and HOBt monohydrate (0.33 g) were added to the thus obtained dichloromethane solution of Leu-Arg(Ts)-Pro-NHEt, the reaction solution was cooled with ice. Then, EDC hydrochloride (0.42 g) was added thereto, and the resulting mixture was stirred for 1 hour. Subsequently, the temperature of the mixture was raised to room temperature and the mixture was stirred for 15 hours, thereby performing a condensation reaction (reaction conversion ratio: 100.0%).

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
  6. temperaturethe reaction solution was cooled with ice
  7. stirringthe resulting mixture was stirred for 1 hour
  8. temperatureSubsequently, the temperature of the mixture was raised to room temperature
  9. stirringthe mixture was stirred for 15 hours
  10. customa condensation reaction (reaction conversion ratio: 100.0%)

Sources & evidence

ORD record
ord-51863082633841f4bba1a33a8bd75953
Source dataset
uspto-grants-2016_05
Patent number
US09346850B2

Linked notes

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