HCID 178445897, compound → HCID 178445914, compound

HRID 464897Notes

Reaction equation

HRID 464897 reaction equation
C([O:8]C(N1C(C(N(C(=O)[C@H](CC2N=CNC=2)N)N)=O)CC2C3C(=CC=CC=3)NC=2C1)=O)C1C=CC=CC=1.[CH2:38]([O:45][C:46]([N:48]1[CH:60]([C:61]([NH:63][C@H:64]([C:71]([NH:73][C@H:74]([CH:79]=NNC(N)=O)[CH2:75][CH:76]([CH3:78])[CH3:77])=[O:72])[CH2:65][C:66]2[N:70]=[CH:69][NH:68][CH:67]=2)=[O:62])[CH2:59][C:58]2[C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[NH:51][C:50]=2[CH2:49]1)=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[CH2:38]([O:45][C:46]([N:48]1[CH:60]([C:61]([NH:63][C@H:64]([C:71]([NH:73][C@H:74]([CH:79]=[O:8])[CH2:75][CH:76]([CH3:78])[CH3:77])=[O:72])[CH2:65][C:66]2[N:70]=[CH:69][NH:68][CH:67]=2)=[O:62])[CH2:59][C:58]2[C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[NH:51][C:50]=2[CH2:49]1)=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

3

Reactant 2

HCID 178445897HCID 178445897, compoundHCID 178511796HCID 178511796, compound

Product 1

HCID 178445914HCID 178445914, compound

Procedure

The procedure described in Example 1(a) was repeated, but using 125 mg. (0.25 mmole) of N-(2-benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carbolin-3-ylcarbonyl)-L-histidine hydrazide. There were obtained 120 mg. of N-(2-benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carbolin-3-ylcarbonyl)-L-histidyl-L-leucinal semicarbazone. This product was then treated in the same way as in Example 1(b) by partition chromatography using Sephadex G-25, to give 67 mg. of the desired compound as a white powdery solid, melting at 126°-130° C.; [α]22 +21.6° (C`0.5, methanol).

Workup

  1. customThere were obtained 120 mg
  2. additionThis product was then treated in the same way as in Example 1(b)
  3. customby partition chromatography
  4. customto give 67 mg

Sources & evidence

ORD record
ord-803c8e24cfbc4cb9b1ebdc7a78ab79ff
Source dataset
uspto-grants-1985_10
Patent number
US04548926

Reaction notes

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