Methanesulfonic Acid → HCID 178465170, compound

HRID 529428Notes

Reaction equation

HRID 529428 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:36]([N:38]1[CH2:47][CH2:46][CH2:45][C@H:39]1[C:40]([NH:42][CH2:43][CH3:44])=[O:41])=[O:37])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:35])[NH:24][S:25]([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:55](C(OC(C)(C)C)=O)[C@H:56]([C:72]([OH:74])=O)[CH2:57][C:58]1[CH:63]=[CH:62][C:61]([O:64][CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)=[CH:60][CH:59]=1.CS(O)(=O)=O.[C:87](=[O:90])([O-])[O-:88].[Na+].[Na+]>ClCCl>[NH:55]([C:87]([O:88][C:4]([CH3:6])([CH3:5])[CH3:3])=[O:90])[C@H:56]([C:72]([NH:1][C@@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:36]([N:38]1[CH2:47][CH2:46][CH2:45][C@H:39]1[C:40]([NH:42][CH2:43][CH3:44])=[O:41])=[O:37])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:35])[NH:24][S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:32])=[CH:33][CH:34]=1)(=[O:27])=[O:26])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:74])[CH2:57][C:58]1[CH:59]=[CH:60][C:61]([O:64][CH2:65][C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=2)=[CH:62][CH:63]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 178465172HCID 178465172, compound

Product 1

HCID 178465170HCID 178465170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-Tyr(Bn)-D-Leu-Leu-Arg(Ts)-Pro-NHEt was prepared from Boc-D-Leu-Leu-Arg(Ts)-Pro-NHEt obtained in Example 2 and Boc-Tyr(Bn) by the same procedure as Example 2. To a solution composed of this compound (0.46 g) and dichloromethane (5 ml), methanesulfonic acid (0.42 g) was added at room temperature, and the resulting mixture was stirred at room temperature for 1 hour, thereby the Boc group was removed (reaction conversion ratio: 99.9%). After the reaction, 5% aqueous sodium carbonate solution (5 ml) was added thereto, and the resulting mixture was stirred for 15 minutes, and then, the aqueous layer was separated off. After Boc-Ser (Bn) (0.19 g) and HOBt monohydrate (0.12 g) were added to the obtained dichloromethane solution of Tyr(Bn)-D-Leu-Leu-Arg(Ts)-Pro-NHEt, the reaction solution was cooled with ice. Then, EDC hydrochloride (0.15 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 a condensation reaction was carried out (reaction conversion ratio: 99.9%).

Workup

  1. additionwas added at room temperature
  2. customthe Boc group was removed
  3. custom(reaction conversion ratio: 99.9%)
  4. additionwas added
  5. stirringthe resulting mixture was stirred for 15 minutes
  6. customthe aqueous layer was separated off
  7. additionAfter Boc-Ser (Bn) (0.19 g) and HOBt monohydrate (0.12 g) were added to the obtained dichloromethane solution of Tyr(Bn)-D-Leu-Leu-Arg(Ts)-Pro-NHEt
  8. temperaturethe reaction solution was cooled with ice
  9. additionThen, EDC hydrochloride (0.15 g) was added
  10. stirringthe resulting mixture was stirred for 1 hour
  11. temperatureSubsequently, the temperature of the mixture was raised to room temperature
  12. stirringthe mixture was stirred for 15 hours
  13. customa condensation reaction
  14. custom(reaction conversion ratio: 99.9%)

Sources & evidence

ORD record
ord-21ea7e1a3ec8420aa97d40f0da5b38af
Source dataset
uspto-grants-2016_05
Patent number
US09346850B2

Reaction notes

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