Dicyclohexylcarbodiimide → tert-butyl (2RS,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]-acetyl}-5-phenylprolinate

HRID 976004Notes

Reaction equation

HRID 976004 reaction equation
C(C(C1C=C([NH:16][C:17](=[O:40])[NH:18][CH2:19][C:20]([N:22]2[CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:32][CH2:31][CH:23]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:21])C=CC=1)=O)C1C=CC=CC=1.CC1C=C(C2NC(C(OC(C)(C)C)=O)CC2)C=CC=1.[CH2:60]([O:67][C:68]([C:70]1[CH:71]=[C:72](NC(=O)NCC(O)=O)[CH:73]=[CH:74][CH:75]=1)=[O:69])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH2:60]([O:67][C:68]([C:70]1[CH:75]=[C:74]([NH:16][C:17](=[O:40])[NH:18][CH2:19][C:20]([N:22]2[CH:33]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:32][CH2:31][CH:23]2[C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])=[O:21])[CH:73]=[CH:72][CH:71]=1)=[O:69])[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 197003762-[3-(3-Benzyloxycarbonylphenyl)-ureido]acetic acidHCID 131719912tert-Butyl (2RS,5SR)-1-{2-[3-(3-benzylcarbonylphenyl)ureido]acetyl}-5-phenylprolinateHCID 131719913tert-butyl (2RS,5SR)-5-(3-methylphenyl)-prolinate

Product 1

HCID 76139539tert-butyl (2RS,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]-acetyl}-5-phenylprolinate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl (2RS,5SR)-1-{2-[3-(3-benzylcarbonylphenyl)ureido]acetyl}-5-phenylprolinate may be prepared as described in Example 41 §A, but starting from 0.4 g of tert-butyl (2RS,5SR)-5-(3-methylphenyl)-prolinate, 0.5 g of 2-[3-(3-benzyloxycarbonylphenyl)-ureido]acetic acid and 0.31 g of N,N'-dicyclohexyl-carbodiimide in 20 cm3 of acetonitrile. After treatment, 0.8 g of tert-butyl (2RS,5RS)-1-{2-[3-(3-benzyloxycarbonylphenyl)ureido]-acetyl}-5-phenylprolinate is obtained in the form of a meringue-like product, used as it is in the subsequent syntheses.

Sources & evidence

ORD record
ord-3b4e2285f0724b16acdbfea544328a51
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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