Hydrochloric Acid → HCID 178427539, compound

HRID 722989Notes

Reaction equation

HRID 722989 reaction equation
Cl.[NH2:2][C@H:3]([C:21]([N:23]1[CH2:62][CH2:61][CH2:60][C@H:24]1[C:25]([NH:27][C@H:28]([C:30]([NH:32][C@H:33]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=1[Cl:45])=[O:40])=[O:31])[CH3:29])=[O:26])=[O:22])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:20])[NH:9][S:10]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[CH3:63][C:64]([O:67][C:68]([NH:70][C@H:71]([C:77](OC1C=CC([N+]([O-])=O)=CC=1)=[O:78])[CH2:72][CH2:73][C:74]([NH2:76])=[O:75])=[O:69])([CH3:66])[CH3:65].C(Cl)(Cl)Cl.CO>O1CCCC1>[NH:70]([C:68]([O:67][C:64]([CH3:66])([CH3:65])[CH3:63])=[O:69])[C@H:71]([C:77]([NH:2][C@H:3]([C:21]([N:23]1[CH2:62][CH2:61][CH2:60][C@H:24]1[C:25]([NH:27][C@H:28]([C:30]([NH:32][C@H:33]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:49]=[CH:48][CH:47]=[CH:46][C:44]=1[Cl:45])=[O:40])=[O:31])[CH3:29])=[O:26])=[O:22])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:20])[NH:9][S:10]([C:13]1[CH:14]=[CH:15][C:16]([CH3:17])=[CH:18][CH:19]=1)(=[O:11])=[O:12])=[O:78])[CH2:72][CH2:73][C:74](=[O:75])[NH2:76]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 7017891L-Glutamine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl esterHCID 21584188Chloroform methanolHCID 178427560Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl2×

Product 1

HCID 178427539HCID 178427539, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C. the solution of 467 mg (0.51 mmol) of HCl.Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12) in 20 ml of anhydrous tetrahydrofuran was adjusted to pH 9, to which he pre-cold solution of 195 mg, (0.53 mmol) of Boc-Gln-Onp in 10 ml of anhydrous tetrahydrofuran was added. The reaction mixture was stirred at room temperature for 96 h and TLC (chloroform/methanol, 9:1) indicated complete disappearance of HCl.Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12). The reaction mixture was evaporated to dryness and the residue was purified on sinica gel chromatography (CHCl3/CH3OH, 10:1) to provide 450 mg (80%) of the title compound as a glassy mass. Mp 80–82° C., FAB-MS (m/e) 1111.3[M+H]+, 1132.5[M+Na]+,1010.0[M-Boc]+.

Workup

  1. customAt 0° C.
  2. additionwas added
  3. customThe reaction mixture was evaporated to dryness
  4. customthe residue was purified on sinica gel chromatography (CHCl3/CH3OH, 10:1)

Sources & evidence

ORD record
ord-6ecd985ec1604a50b227e72a4313fe6a
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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