Hydrochloric Acid → HCID 178427541, compound

HRID 722990Notes

Reaction equation

HRID 722990 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].[NH:63]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[C@H:64]([C:69](OC1C=CC([N+]([O-])=O)=CC=1)=[O:70])[CH2:65][C:66](=[O:68])[NH2:67].C(Cl)(Cl)Cl.CO>O1CCCC1>[NH:63]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[C@H:64]([C:69]([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:70])[CH2:65][C:66](=[O:68])[NH2:67]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 439663L-Asparagine, N2-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl esterHCID 21584188Chloroform methanolHCID 178427560Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl2×

Product 1

HCID 178427541HCID 178427541, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C. the solution of 1160 mg (1.26 mmol) of HCl.Arg(Tos)-Pro-Ala-Lys(ClZ)-OBzl (SEQ ID NO: 12) in 50 ml of anhydrous tetrahydrofuran was adjusted to pH 9, to which the pre-cold solution of 500 mg (1.41 mmol) of Boc-Asn-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 800 mg (57%) of the title compound as a glassy mass. Mp 86–88° C., FAB-MS (m/e) 1097[M+H]+.

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-004f31ff12634fc7b4404f1bc0a82183
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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