Hydrochloric Acid → HCID 178512914, compound

HRID 1586698Notes

Reaction equation

HRID 1586698 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].Cl.Cl.[NH:25]1[CH2:65][CH2:64][CH2:63][C@H:26]1[C:27]([NH:29][C@H:30]([C:42]([N:44]1[CH2:62][CH2:61][CH2:60][C@H:45]1[C:46]([NH:48][C@H:49]([C:57]([NH2:59])=[O:58])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:47])=[O:43])[CH2:31][C:32](=[O:41])[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:28].CN1CCOCC1.C(P(=O)(OCC)OCC)#N>CC(N(C)C)=O>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:25]1[CH2:65][CH2:64][CH2:63][C@H:26]1[C:27]([NH:29][C@H:30]([C:42]([N:44]1[CH2:62][CH2:61][CH2:60][C@H:45]1[C:46]([NH:48][C@H:49]([C:57]([NH2:59])=[O:58])[CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:47])=[O:43])[CH2:31][C:32](=[O:41])[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:28])=[O:12])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 76257Diethyl cyanophosphonateHCID 131717956HCID 131717956, compoundHCID 178479461HCID 178479461, compound

Product 1

HCID 178512914HCID 178512914, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

To a stirred solution of Z-Arg.HCl (5.17 g, 15 mmoles) in dimethylacetamide (25 mL) at 25° C. was added a solution of HCl.Pro-Asp(OBzl)-Pro-Phe-NH2 and N-methylmorpholine (1.65 mL, 15 mmoles) in dimethylacetamide (25 mL). To the resulting solution, diethyl cyanophosphonate (2.45 g, 15 mmoles) and N-methylmorpholine (1.65 mL, 15 mmoles) were added and the mixture stirred for 4 hours. The reaction was quenched by the addition of 10% aqueous acetic acid (10 mL) and the solvents were removed on a rotary evaporator under reduced pressure. The resulting solid was triturated with 10% potassium carbonate and then with water and filtered.

Workup

  1. customThe reaction was quenched by the addition of 10% aqueous acetic acid (10 mL)
  2. customthe solvents were removed on a rotary evaporator under reduced pressure
  3. customThe resulting solid was triturated with 10% potassium carbonate
  4. filtrationwith water and filtered

Sources & evidence

ORD record
ord-7063b66ad009401b83fe6892fd7225c1
Source dataset
uspto-grants-1993_06
Patent number
US05215964

Reaction notes

Loading…