4-Chlorophenyl Isocyanate → tert-butyl (2RS,5SR)-1-{2-[3-(4-chlorophenyl)ureido]acetyl}-5-phenylprolinate

HRID 975999Notes

Reaction equation

HRID 975999 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1.[K+].[Br-]>O1CCCC1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:32])[NH:1][CH2:2][C:3]([N:5]2[CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:14][CH:6]2[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 253877Potassium BromideHCID 18928063HCID 18928063, compound

Product 1

HCID 131719911tert-butyl (2RS,5SR)-1-{2-[3-(4-chlorophenyl)ureido]acetyl}-5-phenylprolinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The operation is carried out in a fashion similar to that described in Example 2, but starting from 1.12 g of tert-butyl (2RS,5SR)-1-(2-aminoacetyl)-5-phenylprolinate and 1.3 cm3 of para-chlorophenyl isocyanate in 50 cm3 of tetrahydrofuran. After treatment, 1.2 g of tert-butyl (2RS,5SR)-1-{2-[3-(4-chlorophenyl)ureido]acetyl}-5-phenylprolinate are obtained in the form of an amorphous solid [proton NMR (250 MHz, DMSO D6, δ in ppm), 1.50 (s, 9H, (CH3)3); 1.85 (m, 2H, CH2); 2.2 and 2.4 (2m, 2H, CH2); 3.25 and 3.85 (ABX, 2H, CH2N); 4.30 (dd, 1H, CHN); 5.20 (dd, 1H, CHN); 6.3 (t, 1H exchangeable, NH); 7.2 to 7.6 (m, 9H, aromatic); 9 (s, 1H exchangeable, NH)], [infrared spectrum (KBr), characteristic bands in cm-1 3370, 3065, 3030, 2980, 2930, 287, 1735, 1595, 1490, 1450, 1545, 1365, 1150, 830, 760, 700].

Sources & evidence

ORD record
ord-7bf4d2a6cde048109b4809f07d0421f1
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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