Benzyloxycarbonyl-asparagine → {(S)-1-[1-Benzyl-3-((S)-2-benzyloxycarbonylamino-3-carbamoyl-propanoylamino)-2-hydroxy-4-phenyl-butylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl ester

HRID 1379359Notes

Reaction equation

HRID 1379359 reaction equation
[NH:1]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C@H:2]([C:7](O)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].NC(CC1C=CC=CC=1)C(O)C(NC(OC(C)(C)C)=O)CC1C=CC=CC=1.[NH2:47][CH:48]([CH:56]([OH:84])[CH:57]([NH:65][C:66](=[O:83])[C@H:67]([CH2:79][C:80](=[O:82])[NH2:81])[NH:68][C:69]([O:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)=[O:70])[CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>CO.C(Cl)(Cl)Cl>[C:69]([NH:68][C@H:67]([C:66]([NH:65][CH:57]([CH:56]([OH:84])[CH:48]([NH:47][C:7](=[O:8])[C@H:2]([CH2:3][C:4](=[O:6])[NH2:5])[NH:1][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:49][C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1)[CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:83])[CH2:79][C:80](=[O:82])[NH2:81])([O:71][CH2:72][C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)=[O:70]

Participants

5

Reactant 3

HCID 75314Benzyloxycarbonyl-asparagineHCID 147043774-Amino-2-(t-butyloxycarbonylamino)-1,5-diphenyl-3-hydroxypentaneHCID 228455872-Amino-4-(Cbz-asparaginyl-amino)-1,5-diphenyl-3-hydroxypentane

Product 1

HCID 3011025{(S)-1-[1-Benzyl-3-((S)-2-benzyloxycarbonylamino-3-carbamoyl-propanoylamino)-2-hydroxy-4-phenyl-butylcarbamoyl]-2-carbamoyl-ethyl}-carbamic acid benzyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Using the procedure of Example 55 but replacing Cbz-Val-OH with Cbz-Asn-OH and replacing the resultant compound of Example 11 with the resultant compound of Example 67 gave, after silica gel chromatography using methanol/chloroform, the desired compound (RF 0.4; 2.5% methanol/2% isopropylamine/chloroform) in 75% yield, m.p. 234°-236° C. (dec). Mass spectrum (M+H)+ =767.

Workup

  1. customgave

Sources & evidence

ORD record
ord-db7bbc4198de4594b098d0e6562a42f1
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

Loading…