N-t-Butoxycarbonyl Statine benzyl ester → HCID 178445976, compound

HRID 255615Notes

Reaction equation

HRID 255615 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36]N)=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(N[C@@H:46]([CH2:60][CH:61]([CH3:63])[CH3:62])[C@@H:47]([OH:59])[CH2:48][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=O)(C)(C)C>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@@H:46]([CH2:60][CH:61]([CH3:63])[CH3:62])[C@@H:47]([OH:59])[CH2:48][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 13961447N-t-Butoxycarbonyl Statine benzyl esterHCID 178514450HCID 178514450, compound

Product 1

HCID 178445976HCID 178445976, compoundYield 26.8%

Procedure

The procedure described in Example 1(c) was repeated, but using 300 mg (0.6 mmole) of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidine hydrazide and 180 mg of benzyl 4(S)-t-butoxycarbonylamino-3(S)-hydroxy-6-methylheptanoate. The resulting syrup was purified by silica gel column chromatography eluted with mixtures of chloroform and methanol ranging from 20:1 to 5:1. The solvent was removed by distillation under reduced pressure from the active fractions, and diethyl ether was added to the residue, to solidify it. This solid was finely pulverized and separated by filtration, giving 97 mg of the title compound as a white powdery solid, melting at 102°-109° C., [α]24 -31.0° (C=0.5 methanol).

Workup

  1. customThe resulting syrup was purified by silica gel column chromatography
  2. washeluted with mixtures of chloroform and methanol ranging from 20:1 to 5:1
  3. customThe solvent was removed by distillation under reduced pressure from the active fractions, and diethyl ether
  4. additionwas added to the residue
  5. customseparated by filtration

Sources & evidence

ORD record
ord-9a9bee7e5ad74180a367395e9284c9fb
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

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