Fmoc-Gly-OH → Acat-IN-5

HRID 2289691Notes

Reaction equation

HRID 2289691 reaction equation
C1C2C(COC([NH:18][CH2:19][C:20](O)=[O:21])=O)C3C(=CC=CC=3)C=2C=CC=1.NC1C=C(C(C)C)C(OS(=O)(=O)NC(=O)CC2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)=C(C(C)C)C=1.[NH2:59][CH:60]=[C:61]1[CH:66]=[C:65]([CH:67]([CH3:69])[CH3:68])[C:64]([O:70][S:71](=[O:92])(=[O:91])[NH:72][C:73](=[O:90])[CH2:74][C:75]2[C:80]([CH:81]([CH3:83])[CH3:82])=[CH:79][C:78]([CH:84]([CH3:86])[CH3:85])=[CH:77][C:76]=2[CH:87]([CH3:89])[CH3:88])=[C:63]([CH:93]([CH3:95])[CH3:94])[CH2:62]1>N1CCCCC1.CN(C)C=O>[NH2:18][CH2:19][C:20]([NH:59][CH2:60][C:61]1[CH:62]=[C:63]([CH:93]([CH3:95])[CH3:94])[C:64]([O:70][S:71](=[O:91])(=[O:92])[NH:72][C:73](=[O:90])[CH2:74][C:75]2[C:76]([CH:87]([CH3:89])[CH3:88])=[CH:77][C:78]([CH:84]([CH3:85])[CH3:86])=[CH:79][C:80]=2[CH:81]([CH3:82])[CH3:83])=[C:65]([CH:67]([CH3:68])[CH3:69])[CH:66]=1)=[O:21]

Participants

5

Reactant 3

HCID 93124Fmoc-Gly-OHHCID 10142595Acat-IN-2HCID 53945870[(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(aminomethylene)-2,6-diisopropyl-phenyl ester

Product 1

HCID 10121195Acat-IN-5

Reagents, catalysts & solvents 1

HCID 23501187piperidine N,N-dimethylformamideSolvent

Procedure

When in the procedure of Example 1, bis-N,N'-(t-butoxycarbonyl)-(S)-lysine is replaced with N-(9-fluorenylmethyoxycarbonyl)-glycine, [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 4-amino-2,6-diisopropyl-phenyl ester is replaced by [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 4-(aminomethylene)-2,6-diisopropyl-phenyl ester, and the crude product is stirred in 20% piperidine/N,N-dimethylformamide for 0.5 hours followed by trituration with hexanes, the title compound is obtained; mp 193-195° C.

Sources & evidence

ORD record
ord-31342828ce694064beef1299d3976f51
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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