Hydrochloric Acid → HCID 15126588, compound

HRID 2294694Notes

Reaction equation

HRID 2294694 reaction equation
C[O:2][C:3](=[O:42])[C@H:4]([CH2:24][C:25]1[N:29]=[CH:28][N:27]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:31]=2[N+:39]([O-:41])=[O:40])[CH:26]=1)[NH:5][C:6](=[O:23])[C@@H:7]([CH2:15][S:16]([C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:18])=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>O1CCOCC1>[C:19]([S:16]([CH2:15][C@@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:6]([NH:5][C@H:4]([C:3]([OH:42])=[O:2])[CH2:24][C:25]1[N:29]=[CH:28][N:27]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:31]=2[N+:39]([O-:41])=[O:40])[CH:26]=1)=[O:23])(=[O:18])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22845095HCID 22845095, compound

Product 1

HCID 15126588HCID 15126588, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

20.5 g (34.07 mmol) of N-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamoyl]-1-(2,4-dinitrophenyl)-L-histidine methyl ester are dissolved in 180 ml of dioxan, treated with 85 ml (170.34 mmol) of 2N hydrochloric acid and subsequently heated to 80° for 2.5 hours. Usual working-up and crystallization from ether/hexane yields 15.7 g (78%) of N-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamoyl]-1-(2,4-dinitrophenyl)-L-histidine in the form of a pale yellow amorphous solid, Rf value 0.2 in a 5:1 mixture of methylene chloride and methanol, MS: 588 (M+H)+.

Workup

  1. temperaturesubsequently heated to 80° for 2.5 hours
  2. customcrystallization from ether/hexane

Sources & evidence

ORD record
ord-bede7a80b3384844a16c54c7fa0ff322
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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