HCID 178501387, compound → HCID 178476673, compound

HRID 904964Notes

Reaction equation

HRID 904964 reaction equation
[NH:1]([C:66]([O:68][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)=[O:67])[C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:39]([NH:41][C@H:42]([C:46]([NH:48][C@H:49]([C:62]([O:64][CH3:65])=[O:63])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57]C(C)(C)C)=[CH:53][CH:52]=1)=[O:47])[CH:43]([CH3:45])[CH3:44])=[O:40])[CH2:30][CH2:31][C:32](=[O:38])[O:33]C(C)(C)C)=[O:27])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:25])[NH2:24])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OC(C)(C)C)=O.Cl>FC(F)(F)C(O)=O>[NH:1]([C:66]([O:68][CH2:69][C:70]1[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=1)=[O:67])[C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:29]([C:39]([NH:41][C@H:42]([C:46]([NH:48][C@H:49]([C:62]([O:64][CH3:65])=[O:63])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([OH:57])=[CH:53][CH:52]=1)=[O:47])[CH:43]([CH3:45])[CH3:44])=[O:40])[CH2:30][CH2:31][C:32](=[O:33])[OH:38])=[O:27])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:24])[NH2:25])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH3:31][C:32]([OH:38])=[O:33]

Participants

3

Reactant 1

HCID 178501387HCID 178501387, compound

Product 1

HCID 178476673HCID 178476673, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.2 g (1.1 mmoles) of Z-Lys(Boc)-Arg-Glu(OBut)-Val-Tyr(But)-OMe.HCl are dissolved in 10 ml of 90 percent strength trifluoroacetic acid. The mixture is allowed to stand for one hour at room temperature and is concentrated. The residue is partitioned between 150 ml of water and 100 ml of diethyl ether. The aqueous phase is stirred with a weakly basic ion exchanger in the acetate form. The exchanger is filtered off and the filtrate is freeze-dried. Yield 880 mg (89%), [α]D23 =-45.8° (c=1, in water).

Workup

  1. concentrationis concentrated
  2. customThe residue is partitioned between 150 ml of water and 100 ml of diethyl ether
  3. filtrationThe exchanger is filtered off
  4. customthe filtrate is freeze-dried
  5. customYield 880 mg (89%), [α]D23 =-45.8° (c=1, in water)

Sources & evidence

ORD record
ord-54e5e0766c8640959e98d24206f3ae0d
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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